PGP Desktop Instruction Manual

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PGP® Desktop for Mac OS X

User's Guide

Version Information

PGP Desktop for Macintosh OS X User's Guide. PGP Desktop Version 10.1.2. Released March 2011.

Copyright © 2011 by PGP Corporation. All Rights Reserved. No part of this document can be reproduced or transmitted in any form or by any means, electronic or mechanical, for any purpose, without the express written permission of PGP Corporation.

Trademark Information

PGP, Pretty Good Privacy, and the PGP logo are registered trademarks of PGP Corporation in the US and other countries. IDEA is a trademark of Ascom Tech AG. Windows and ActiveX are registered trademarks of Microsoft Corporation. AOL is a registered trademark, and AOL Instant Messenger is a trademark, of America Online, Inc. Red Hat and Red Hat Linux are trademarks or registered trademarks of Red Hat, Inc. Linux is a registered trademark of Linus Torvalds. Solaris is a trademark or registered trademark of Sun Microsystems, Inc. AIX is a trademark or registered trademark of International Business Machines Corporation. HP-UX is a trademark or registered trademark of Hewlett-Packard Company. SSH and Secure Shell are trademarks of SSH Communications Security, Inc. Rendezvous and Mac OS X are trademarks or registered trademarks of Apple Computer, Inc. All other registered and unregistered trademarks in this document are the sole property of their respective owners.

Licensing and Patent Information

The IDEA cryptographic cipher described in U.S. patent number 5,214,703 is licensed from Ascom Tech AG. The CAST-128 encryption algorithm, implemented from RFC 2144, is available worldwide on a royalty-free basis for commercial and non-commercial uses. PGP Corporation has secured a license to the patent rights contained in the patent application Serial Number 10/655,563 by The Regents of the University of California, entitled Block Cipher Mode of Operation for Constructing a Wide-blocksize block Cipher from a Conventional Block Cipher. Some third-party software included in PGP Universal Server is licensed under the GNU General Public License (GPL). PGP Universal Server as a whole is not licensed under the GPL. If you would like a copy of the source code for the GPL software included in PGP Universal Server, contact PGP Support (https://support.pgp.com). PGP Corporation may have patents and/or pending patent applications covering subject matter in this software or its documentation; the furnishing of this software or documentation does not give you any license to these patents.

Acknowledgments

This product includes or may include:

-- The Zip and ZLib compression code, created by Mark Adler and Jean-Loup Gailly, is used with permission from the free Info-ZIP implementation, developed by zlib (http://www.zlib.net). -- Libxml2, the XML C parser and toolkit developed for the Gnome project and distributed and copyrighted under the MIT License found at http://www.opensource.org/licenses/mit-license.html. Copyright © 2007 by the Open Source Initiative. -- bzip2 1.0, a freely available high-quality data compressor, is copyrighted by Julian Seward, © 1996-2005. -- Application server (http://jakarta.apache.org/), web server (http://www.apache.org/), Jakarta Commons (http://jakarta.apache.org/commons/license.html) and log4j, a Java-based library used to parse HTML, developed by the Apache Software Foundation. The license is at www.apache.org/licenses/LICENSE-2.0.txt. -- Castor, an open-source, data-binding framework for moving data from XML to Java programming language objects and from Java to databases, is released by the ExoLab Group under an Apache 2.0-style license, available at http://www.castor.org/license.html. -- Xalan, an open-source software library from the Apache Software Foundation that implements the XSLT XML transformation language and the XPath XML query language, is released under the Apache Software License, version 1.1, available at http://xml.apache.org/xalan-j/#license1.1. -- Apache Axis is an implementation of the SOAP ("Simple Object Access Protocol") used for communications between various PGP products is provided under the Apache license found at

http://www.apache.org/licenses/LICENSE-2.0.txt. -- mx4j, an open-source implementation of the Java Management Extensions (JMX), is released

under an Apache-style license, available at http://mx4j.sourceforge.net/docs/ch01s06.html. -- jpeglib version 6a is based in part on the work of the Independent JPEG Group. (http://www.ijg.org/) -- libxslt the XSLT C library developed for the GNOME project and used for XML transformations is distributed under the MIT License http://www.opensource.org/licenses/mit-license.html. -- PCRE Perl regular expression compiler, copyrighted and distributed by University of Cambridge. ©1997-2006. The license agreement is at http://www.pcre.org/license.txt. -- BIND Balanced Binary Tree Library and Domain Name System (DNS) protocols developed and copyrighted by Internet Systems Consortium, Inc. (http://www.isc.org) -- Free BSD implementation of daemon developed by The FreeBSD Project, © 1994-2006. -- Simple Network Management Protocol Library developed and copyrighted by Carnegie Mellon University © 1989, 1991, 1992, Networks Associates Technology, Inc, © 2001- 2003, Cambridge Broadband Ltd. © 2001- 2003, Sun Microsystems, Inc., © 2003, Sparta, Inc, © 2003-2006, Cisco, Inc and Information Network Center of Beijing University of Posts and Telecommunications, © 2004. The license agreement for these is at http://net-snmp.sourceforge.net/about/license.html. -- NTP version 4.2 developed by Network Time Protocol and copyrighted to various contributors. -- Lightweight Directory Access Protocol developed and copyrighted by OpenLDAP Foundation. OpenLDAP is an open-source implementation of the Lightweight Directory Access Protocol (LDAP). Copyright © 1999-2003, The OpenLDAP Foundation. The license agreement is at http://www.openldap.org/software/release/license.html. Secure shell OpenSSH developed by OpenBSD project is released by the OpenBSD Project under a BSD-style license, available at

http://www.openbsd.org/cgi-bin/cvsweb/src/usr.bin/ssh/LICENCE?rev=HEAD. -- PC/SC Lite is a free implementation of PC/SC, a specification for

SmartCard integration is released under the BSD license. -- Postfix, an open source mail transfer agent (MTA), is released under the IBM Public License

1.0, available at http://www.opensource.org/licenses/ibmpl.php. -- PostgreSQL, a free software object-relational database management system, is released under a BSD-style license, available at http://www.postgresql.org/about/licence. -- PostgreSQL JDBC driver, a free Java program used to connect to a PostgreSQL database using standard, database independent Java code, (c) 1997-2005, PostgreSQL Global Development Group, is released under a BSD-style license, available at http://jdbc.postgresql.org/license.html. -- PostgreSQL Regular Expression Library, a free software object-relational database management system, is released under a BSD-style license, available at http://www.postgresql.org/about/licence. --

21.vixie-cron is the Vixie version of cron, a standard UNIX daemon that runs specified programs at scheduled times. Copyright © 1993, 1994 by Paul Vixie; used by permission. -- JacORB, a Java object used to facilitate communication between processes written in Java and the data layer, is open source licensed under the GNU Library General Public License (LGPL) available at http://www.jacorb.org/lgpl.html. Copyright © 2006 The JacORB Project. -- TAO (The ACE ORB) is an open-source implementation of a CORBA Object Request Broker (ORB), and is used for communication between processes written in C/C++ and the data layer. Copyright (c) 1993-2006 by Douglas C. Schmidt and his research group at Washington University, University of California, Irvine, and Vanderbilt University. The open source software license is available at

http://www.cs.wustl.edu/~schmidt/ACE-copying.html. -- libcURL, a library for downloading files via common network services, is open source software

provided under a MIT/X derivate license available at http://curl.haxx.se/docs/copyright.html. Copyright (c) 1996 - 2007, Daniel Stenberg. -- libuuid, a library used to generate unique identifiers, is released under a BSD-style license, available at

line options, is released under the terms of the GNU Free Documentation License available at http://directory.fsf.org/libs/COPYING.DOC. Copyright © 2000-2003 Free Software Foundation, Inc. -- gSOAP, a development tool for Windows clients to communicate with the Intel Corporation AMT chipset

on a motherboard, is distributed under the gSOAP Public License version 1.3b, available at http://www.cs.fsu.edu/~engelen/license.html. -- Windows Template Library (WTL) is used for developing user interface components and is distributed under the Common Public License v1.0 found at

http://opensource.org/licenses/cpl1.0.php. -- The Perl Kit provides several independent utilities used to automate a variety of maintenance functions

and is provided under the Perl Artistic License, found at http://www.perl.com/pub/a/language/misc/Artistic.html. -- rEFIt - libeg, provides a graphical interface library for EFI, including image rendering, text rendering, and alpha blending, and is distributed under the license found at

reserved. -- Java Radius Client, used to authenticate PGP Universal Web Messenger users via Radius, is distributed under the Lesser General Public License (LGPL) found at http://www.gnu.org/licenses/lgpl.html. -- Yahoo! User Interface (YUI) library version 2.5.2, a Web UI interface library for AJAX. Copyright (c) 2009, Yahoo! Inc. All rights reserved. Released under a BSD-style license, available at http://developer.yahoo.com/yui/license.html. --

JSON-lib version 2.2.1, a Java library used to convert Java objects to JSON (JavaScript Object Notation) objects for AJAX. Distributed under the

Apache 2.0 license, available at http://json-lib.sourceforge.net/license.html. -- EZMorph, used by JSON-lib, is distributed under the Apache 2.0 license, available at http://ezmorph.sourceforge.net/license.html. -- Apache Commons Lang, used by JSON-lib, is distributed under the Apache 2.0 license, available at http://commons.apache.org/license.html. -- Apache Commons BeanUtils, used by JSON-lib, is distributed under the Apache 2.0 license, available at http://commons.apache.org/license.html. -- SimpleIni is an .ini format file parser and provides the ability to read and write .ini files, a common configuration file format used on Windows, on other platforms. Distributed under the MIT License found at

Standard Template Library functions and data structures and is distributed under the MIT License found at

(protobuf), Google's data interchange format, are used to serialize structure data in the PGP SDK. Distributed under the BSD license found at

Additional acknowledgements and legal notices are included as part of the PGP Universal Server.

Export Information

Export of this software and documentation may be subject to compliance with the rules and regulations promulgated from time to time by the Bureau of Export Administration, United States Department of Commerce, which restricts the export and re-export of certain products and technical data.

Limitations

The software provided with this documentation is licensed to you for your individual use under the terms of the End User License Agreement provided with the software. The information in this document is subject to change without notice. PGP Corporation does not warrant that the information meets your requirements or that the information is free of errors. The information may include technical inaccuracies or typographical errors. Changes may be made to the information and incorporated in new editions of this document, if and when made available by PGP Corporation.

Unsupported Third Party Products

By utilizing third party products, software, drivers, or other components ("Unsupported Third Party Product") to interact with the PGP software and/or by utilizing any associated PGP command or code provided by to you by PGP at its sole discretion to interact with the Unsupported Third Party Product ("PGP Third Party Commands"), you acknowledge that the PGP software has not been designed for or formally tested with the Unsupported Third Party Product, and therefore PGP provides no support or warranties with respect to the PGP Third Party Commands or the PGP software's compatibility with Unsupported Third Party Products. THE PGP THIRD PARTY COMMANDS ARE PROVIDED "AS IS," WITH ALL FAULTS, AND THE ENTIRE RISK AS TO SATISFACTORY QUALITY, PERFORMANCE, ACCURACY, AND EFFORT IS WITH YOU. TO THE MAXIMUM EXTENT PERMITTED BY APPLICABLE LAW, PGP DISCLAIMS ALL REPRESENTATIONS, WARRANTIES, AND CONDITIONS, WHETHER EXPRESS OR IMPLIED, INCLUDING ANY WARRANTIES OR CONDITIONS OF MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE, TITLE, NONINFRINGEMENT, QUIET ENJOYMENT, AND ACCURACY WITH RESPECT TO THE PGP THIRD PARTY COMMANDS OR THE PGP SOFTWARE'S COMPATIBILITY WITH THE UNSUPPORTED THIRD PARTY PRODUCT.

Contents

About PGP Desktop 10.1 for Mac OS X

What's New in PGP Desktop for Mac OS X Version 10.1 1 Using this Guide 3

“Managed” versus “Unmanaged” Users 3

Conventions Used in This Guide 4 Who Should Read This Document 4 About PGP Desktop Licensing 4

About PGP Desktop Licensing 5

Checking License Details 5

If Your License Has Expired 7 Getting Assistance 7

Getting product information 8

Contact Information 8

PGP Desktop Basics 9

PGP Desktop Terminology 9

PGP Product Components 9

Terms Used in PGP Desktop 10 Conventional and Public Key Cryptography 12 Using PGP Desktop for the First Time 13

Installing PGP Desktop 17

System Requirements 17 Installing and Configuring PGP Desktop 17

Installing the Software 17

Using PGP Desktop with Apple Boot Camp 18

Upgrading the Software 19

Licensing PGP Desktop 21

Running the Setup Assistant 21

Integrating with Entourage 2008 22 Uninstalling PGP Desktop 22 Moving Your PGP Desktop Installation from One Computer to Another 23

The PGP Desktop User Interface 25

Accessing PGP Desktop Features 25

PGP Desktop Main Screen 26

Using the PGP Desktop Icon in the Menu Bar 27

Using the PGP Dock Icon 28

Using the Mac OS X Finder 29 PGP Desktop Notifier alerts 30

PGP® Desktop for Mac OS X Contents

PGP Desktop Notifier for Messaging 30 PGP Desktop and the Finder 35

Overview 35

Encrypt, Sign, or Encrypt and Sign 36

Shred 37

Decrypt/Verify 38

Mount or Unmount a PGP Virtual Disk Volume 39

Import a PGP Key 39

Add PGP Public Keys to Your Keyring 40

Extract the Contents of a PGP Zip Archive 40 Viewing the PGP Log 41

Working with PGP Keys 43

Viewing Keys 44

Creating a Smart Keyring 45 Creating a Keypair 46

Expert Mode Key Settings 48 Protecting Your Private Key 49

Protecting Keys and Keyrings 49

Backing up Your Private Key 50

What if You Lose Your Key? 51 Distributing Your Public Key 51

Placing Your Public Key on a Keyserver 52

Including Your Public Key in an Email Message 53

Exporting Your Public Key to a File 53 Getting the Public Keys of Others 54

Getting Public Keys from a Keyserver 54

Getting Public Keys from Email Messages 55 Working with Keyservers 56 Using Master Keys 57

Adding Keys to the Master Key List 57

Deleting Keys from the Master Key List 58

Managing PGP Keys 59

Examining and Setting Key Properties 59 Adding and Removing Photographs 60 Managing User Names and Email Addresses on a Key 61 Importing Keys and X.509 Certificates 62

Importing X.509 Certificates Included in S/MIME Email Messages 63 Changing Your Passphrase 63 Deleting Keys, User IDs, and Signatures 64 Disabling and Enabling Public Keys 65 Verifying a Public Key 65 Signing a Public Key 66

Revoking Your Signature from a Public Key 68 Granting Trust for Key Validations 68

To grant trust to a key 69 Working with Subkeys 69

PGP® Desktop for Mac OS X Contents

Using Separate Subkeys 71

Viewing Subkeys 71

Creating New Subkeys 72

Specifying Key Usage for Subkeys 72

Revoking Subkeys 73

Removing Subkeys 73 Working with ADKs 74

Adding an ADK to a Keypair 74

Updating an ADK 75

Removing an ADK 75 Working with Revokers 75

Appointing a Designated Revoker 76

Revoking a Key 76 Splitting and Rejoining Keys 77

Creating a Split Key 77

Rejoining Split Keys 78 If You Lost Your Key or Passphrase 80

Reconstructing Keys with PGP Universal Server 80

Creating Key Reconstruction Data 80

Reconstructing Your Key if You Lost Your Key or Passphrase 82 Protecting Your Keys 83

Securing Email Messages 85

How PGP Desktop Secures Email Messages 85

Incoming Messages 86

Understanding Annotations on Incoming Messages 87

Outgoing Messages 88

Securing Sent Items on IMAP Email Servers 88 Using Offline Policy 89 Services and Policies 90

Viewing Services and Policies 91

Creating a New Messaging Service 92

Editing Message Service Properties 94

Disabling or Enabling a Service 95

Deleting a Service 95

Multiple Services 96

Troubleshooting PGP Messaging Services 96 Creating a New Security Policy 98

Regular Expressions in Policies 103

Security Policy Information and Examples 105 Working with the Security Policy List 108

Editing a Security Policy 108

Editing a Mailing List Policy 108

Deleting a Security Policy 113

Changing the Order of Policies in the List 113 PGP Desktop and SSL 113 Key Modes 115

Determining Key Mode 116

Changing Key Mode 117

iii

PGP® Desktop for Mac OS X Contents

Viewing the PGP Log 118 Using PGP Scripts with Entourage 2008 119

Securing Instant Messaging 121

About PGP Desktop’s Instant Messaging Compatibility 121

Instant Messaging Client Compatibility 122 About the Keys Used for Encryption 123 Encrypting your IM Sessions 123

Viewing Email with PGP Viewer 125

Overview of PGP Viewer 125

Supported Email Clients 126 Opening an Encrypted Email Message or File 126 Copying Email Messages to Your Inbox 127 Exporting Email Messages 128 PGP Viewer Preferences 128 Security Features in PGP Viewer 129

Protecting Disks with PGP Whole Disk Encryption 131

About PGP Whole Disk Encryption 132

Encrypting Boot Disks 133

How does PGP WDE Differ from PGP Virtual Disk? 134 Licensing PGP Whole Disk Encryption 134

License Expiration 135 Prepare Your Disk for Encryption 135

Supported Disk Types 136

Supported Keyboards 136

Ensure Disk Health Before Encryption 137

Calculate the Encryption Duration 138

Run a Pilot Test to Ensure Software Compatibility 138 Determine the Authentication Method for the Disk 138 Encrypting a Disk 139

Supported Characters 140

Encrypting the Disk 140

Encountering Disk Errors During Encryption 143 Using a PGP-WDE Encrypted Disk 143

Authenticating at the PGP BootGuard Screen 144 Maintaining the Security of Your Disk 145

Viewing Key Information on an Encrypted Disk 145

Modifying the System Partition 145

Adding Other Users to an Encrypted Disk 145

Deleting Users From an Encrypted Disk 146

Changing User Passphrases 147

Re-Encrypting an Encrypted Disk 147

Backing Up and Restoring 148

Uninstalling PGP Desktop from Encrypted Disks 148

PGP® Desktop for Mac OS X Contents

Using PGP WDE in a PGP Universal Server-Managed Environment 149

PGP Whole Disk Encryption Administration 149

Creating a Recovery Token 150

Using a Recovery Token 150 Recovering Data From an Encrypted Drive 151

Creating and Using Recovery Disks 151 Decrypting a PGP WDE-Encrypted Disk 152 Moving Removable Disks to Other Systems 153 Accessing Data on Encrypted Removable Disks 153 Special Security Precautions Taken by PGP Desktop 154

Passphrase Erasure 154

Virtual Memory Protection 154

Memory Static Ion Migration Protection 154

Other Security Considerations 155 Technical Details About Encrypting Boot Disks 156

Using PGP Virtual Disks 157

About PGP Virtual Disks 158 Creating a New PGP Virtual Disk 159 Viewing the Properties of a PGP Virtual Disk 162 Using a Mounted PGP Virtual Disk 162

Mounting a PGP Virtual Disk 163

Unmounting a PGP Virtual Disk 163

Set Mount Location 164

Compacting a PGP Virtual Disk 164

Re-Encrypting PGP Virtual Disks 165 Working with Alternate Users 166

Adding Alternate User Accounts to a PGP Virtual Disk 166

Deleting Alternate User Accounts From a PGP Virtual Disk 166

Disabling and Enabling Alternate User Accounts 167

Changing Read/Write and Read-Only Status 167

Granting Administrator Status to an Alternate User 168 Changing User Passphrases 168 Deleting PGP Virtual Disks 169 Maintaining PGP Virtual Disks 169

Mounting PGP Virtual Disk Volumes on a Remote Server 170

Backing up PGP Virtual Disk Volumes 170

Exchanging PGP Virtual Disks 171 The PGP Virtual Disk Encryption Algorithms 171 Special Security Precautions Taken by PGP Virtual Disk 172

Passphrase Erasure 172

Virtual Memory Protection 173

Memory Static Ion Migration Protection 173

Other Security Considerations 173

Accessing Mobile Data with PGP Portable 175

Accessing Data on a PGP Portable Disk 175

Changing the Passphrase for a PGP Portable Disk 177

PGP® Desktop for Mac OS X Contents

Unmounting a PGP Portable Disk 177

Using PGP Zip 179

Overview 179 Creating PGP Zip Archives 180 Opening a PGP Zip Archive 181 Verifying Signed PGP Zip Archives 182

Shredding Files with PGP Shredder 183

Using PGP Shredder to Permanently Delete Files and Folders 183

Shredding Files using the PGP Shredder icon 184

Shredding Files using the Shred Files Icon in the PGP Desktop Toolbar 185

Shredding Files using the Shred Command from the File menu 185

Shredding Files in the Finder 185

Setting PGP Desktop Preferences 187

Accessing PGP Desktop Preferences 187 General Preferences 188 Keys Preferences 189 Master Keys Preferences 191 Messaging Preferences 192

Proxy Options 194 Disk Preferences 196 Notifications Preferences 198 Advanced Preferences 200

Working with Passwords and Passphrases 201

Choosing whether to use a password or passphrase 201 The Passphrase Quality Bar 202 Creating Strong Passphrases 203 What if You Forget Your Passphrase? 205 Saving Your Passphrase in the Keychain 205

Using PGP Desktop with PGP Universal Server 207

Overview 207 For PGP Administrators 208 Manually binding to a PGP Universal Server 209

Index 211

About PGP Desktop 10.1

for Mac OS X

PGP Desktop is a security tool that uses cryptography to protect your data against unauthorized access.

PGP Desktop protects your data while being sent by email or by instant messaging (IM). It lets you encrypt your entire hard drive or hard drive partition (on Windows systems)—so everything is protected all the time—or just a portion of your hard drive, via a virtual disk on which you can securely store your most sensitive data. You can use it to share your files and folders securely with others over a network. It lets you put any combination of files and folders into an encrypted, compressed package for easy distribution or backup. Finally, use PGP Desktop to shred (securely delete) sensitive files—so that no one can retrieve them—and shred free space on your hard drive, so there are no unsecured remains of any files.

Use PGP Desktop to create PGP keypairs and manage both your personal keypairs and the public keys of others.

To make the most of PGP Desktop, you should be familiar with PGP Desktop Terminology (on page public-key cryptography, as described in Conventional and Public Key Cryptography (on page

9). You should also understand conventional and

12).

In This Chapter

What's New in PGP Desktop for Mac OS X Version 10.1 ........................ 1

Using this Guide ........................................................................................ 3

Who Should Read This Document ............................................................ 4

About PGP Desktop Licensing .................................................................. 4

Getting Assistance .................................................................................... 7

What's New in PGP Desktop for Mac OS X Version 10.1

Building on PGP Corporation’s proven technology, PGP Desktop 10.1 for Mac OS X includes numerous improvements and the following new and resolved features.

PGP® Desktop for Mac OS X About PGP Desktop 10.1 for Mac OS X

Messaging

 Improvements have been made to annotations. In a PGP Universal

Server-managed environment, your administrator can now specify where the email annotation will be, such as end of message rather than wrapped around the message.

 You can now protect sent message copies for IMAP accounts (available for

standalone installations only) to provide additional security so you can protect sensitive emails that you have sent using your IMAP account. Choose to Encrypt, Encrypt and Sign, or Sign Only messages as they are copied to your IMAP Sent Items mailbox.

 In a managed environment, your PGP Universal Server administrator can

set policy to enable you to decide if you want to perform signature verification on email messages. If enabled, a new button and/or menu option appears in your Microsoft Outlook or Lotus Notes email client. The button or option will be in the default state set by your administrator but you can choose to override this setting.

 In a managed environment, your PGP Universal Server administrator may

have specified certain PGP Notifier settings (for example, whether notifications are to be displayed or the location of the notifier).

 X.509 certificates included in an S/MIME email message sent to you can

now be imported to your key ring. The same settings you have specified when public keys are found apply to these certificates. If specified, PGP Desktop extracts and then imports the X.509 certificate to your keyring. If you want to encrypt email using imported certificates, be sure to manually sign the certificate.

 In a managed environment, your PGP Universal Server administrator may

have specified a setting so that additional information is included in the Non-Delivery Receipt when a message is blocked. If PGP Desktop is unable to find a key for one or more of the recipients in a group list, the email addresses are listed in the Error Details of the Non-Delivery Receipt.

PGP Portable

 A link for More Info is now available on the PGP Portable dialog box

displayed when you access data on the device. Your browser launches and the PGP Corporation Support site page is displayed.

 You can now view available disk space and total size of the PGP Portable

Disk once the disk has been mounted. When you move your cursor over the dock item for a few seconds, the PGP Notifier message appears and displays the mount status of the PGP Portable Disk as well as the updated disk space information.

PGP® Desktop for Mac OS X About PGP Desktop 10.1 for Mac OS X

PGP Whole Disk Encryption

 AES-128 and AES-256 cipher algorithm for PGP Desktop for Mac OS X

have been enhanced to improve performance of encryption and decryption times as well as disk access times for encrypted disks.

 Enhancement to force the encryption of boot drives, by policy. This

includes forcing encryption if policy changed (for example, you previously did not have to encrypt boot drives, and your administrator modified policy to require encryption).

Using this Guide

This Guide provides information on configuring and using the components within PGP Desktop. Each chapter of the guide is devoted to one of the components of PGP Desktop.

“Managed” versus “Unmanaged” Users

A PGP Universal Server can be used to control the policies and settings used by components of PGP Desktop. This is often the case in enterprises using PGP software. PGP Desktop users in this configuration are known as managed users, because the settings and policies available in their PGP Desktop software are pre-configured by a PGP administrator and managed using a PGP Universal Server. If you are part of a managed environment, your company may have specific usage requirements. For example, managed users may or may not be allowed to send plaintext email, or may be required to encrypt their disk with PGP Whole Disk Encryption.

Users not under the control of a PGP Universal Server are called unmanaged or standalone users.

This document describes how PGP Desktop works in both situations; however, managed users may discover while working with the product that some of the settings described in this document are not available in their environments. For more information, see Using PGP Desktop with PGP Universal Server (on page

207).

Features Customized by Your PGP Universal Server Administrator

If you are using PGP Desktop as a "managed" user in a PGP Universal Server-managed environment, there are some settings that can be specified by your administrator. These settings may change the way features are displayed in PGP Desktop.

PGP® Desktop for Mac OS X About PGP Desktop 10.1 for Mac OS X

 Disabled features. Your PGP Universal Server administrator can enable or

disable specific functionality. For example, your administrator may disable the ability to create PGP Zip archives, or to create PGP NetShare protected folders (on Windows systems).

When a feature is disabled, the control item in the left side is not displayed and the menu for that feature is not available. The graphics included in this guide depict the default installation with all features enabled. The PGP Desktop interface may look different if your administrator has customized the features available.

Conventions Used in This Guide

Notes, Cautions, and Warnings are used in the following ways.

Notes: Notes are extra, but important, information. A Note calls your

attention to important aspects of the product. You will be able to use the product better if you read the Notes.

Cautions: Cautions indicate the possibility of loss of data or a minor security

breach. A Caution tells you about a situation where problems could occur unless precautions are taken. Pay attention to Cautions.

Warnings: Warnings indicate the possibility of significant data loss or a major

security breach. A Warning means serious problems are going to happen unless you take the appropriate action. Please take Warnings very seriously.

Who Should Read This Document

This document is for anyone who is going to be using the PGP Desktop for Mac OS X software to protect their data.

Note: If you are new to cryptography and would like an overview of the

terminology and concepts in PGP Desktop, see An Introduction to Cryptography (it was installed onto your computer when you installed PGP

Desktop).

About PGP Desktop Licensing

A license is used within the PGP software to enable the functionality you purchased, and sets the expiration of the software. Depending on the license you have, some or all of the PGP Desktop family of applications will be active. Once you have entered the license, you must then authorize the software with PGP Corporation, either manually or online.

PGP® Desktop for Mac OS X About PGP Desktop 10.1 for Mac OS X

There are three types of licenses:

 Evaluation: This type of license is typically time-delimited and may not

include all PGP Desktop functionality.

 Subscription: This type of license is typically valid for a subscription period

of one year. During the subscription period, you receive the current version of PGP software and all upgrades and updates released during this period.

 Perpetual: This type of license allows you to use PGP Desktop indefinitely.

With the addition of the annual Software Insurance policy, which must be renewed annually, you also receive all upgrades and updates released during the policy term.

About PGP Desktop Licensing

To license PGP Desktop Do one of the following:

 If you are a managed user, you are most likely already using a licensed

copy of PGP Desktop. Check your license details as described in Checking License Details (on page administrator.

5). If you have questions, please contact your PGP

 If you are an unmanaged user, or a PGP administrator, check your license

details as described in Checking License Details (on page authorize your copy of PGP Desktop, do so as described in Authorizing PGP Desktop for Mac OS X (see " page

Checking License Details

 To see the details of your PGP Desktop license:

1 Open PGP Desktop.

2 From the PGP menu, select License. The License Information dialog box is

displayed. This dialog box displays:

 Name: The name your license is registered to.

 Organization: The organization your license is registered to.

 Email: The email address associated with your license.

 Type: The type of license you have, Enterprise or Home.

5). If you need to

Authorizing PGP Desktop or Mac OS X" on

6).

PGP® Desktop for Mac OS X About PGP Desktop 10.1 for Mac OS X

3 Click Details. The details of your license are displayed.

 Expiration Date: The date your license expires.

 Number of Seats: The number of seats available for this license.

 Enabled Features: The components that are active in your license.

 Disabled Features: The components that are not active in your

license.

Note: If you do not authorize your copy of PGP Desktop, only limited features

are available to you (PGP Zip and Keys).

Authorizing PGP Desktop or Mac OS X

If you need to change to a new license number, or if you skipped the license authorization process during configuration, follow these instructions to authorize your software.

 Before you begin

If you purchased PGP Desktop, you received an order confirmation with licensing information.

1 OpenPGP Desktop.

2 From the PGP menu, select License.

3 Click Change License.

4 Type the Name and Organization exactly as specified in your order

confirmation.

5 Type the Email address you want to assign to the licensing of the product.

6 Do one of the following:

 Type your 28-character license number in the License Number fields

(for example, DEMO1-DEMO2-DEMO3-DEMO4-DEMO5-ABC).

PGP® Desktop for Mac OS X About PGP Desktop 10.1 for Mac OS X

Note: To avoid typing errors and make the authorization easier, copy the

entire license number, put the cursor in the first “License Number” field, and paste. Your license number will be correctly entered into all six

License Number fields.

 To purchase a PGP Desktop license, select Purchase Now. A Web

browser opens so you can access the online PGP Store.

7 Click Authorize.

8 When your license is authorized, click OK to complete the process.

Resolving License Authorization Errors

If you receive any error messages while authorizing your software, the ways to resolve this issue vary based on the error message. See the HOWTO: License PGP Desktop 10.1 section in the PGP Support Portal ( for suggestions.

https://support.pgp.com)

If Your License Has Expired

If your PGP Desktop license has expired, you will receive a PGP License Expiration message when you launch PGP Desktop. See the following sections for information on how an expired license affects the functionality of PGP Desktop.

PGP Desktop Email

 Outgoing email messages are no longer sent encrypted.

PGP Virtual Disk

 PGP Virtual Disks are still accessible in Read-Only mode. Read-Only allows

data to be copied from a PGP Virtual Disk, however no data can be copied to a PGP Virtual Disk.

PGP Whole Disk Encryption

Any fixed disks that have been encrypted with PGP Desktop are automatically decrypted 90 days after the license expiration date.

Getting Assistance

For additional resources, see these sections.

PGP® Desktop for Mac OS X About PGP Desktop 10.1 for Mac OS X

Getting product information

Unless otherwise noted, online help is installed and is available within the PGP Desktop product. Release notes are also available, which may have last-minute information not found in the product documentation. The users guide and quick start guides, provided as Adobe Acrobat PDF files, are available on the Documentation ( Portal.

Once PGP Desktop is released, additional information regarding the product is entered into the online Knowledge Base available on the PGP Support Portal

Web Site (

https://pgp.custhelp.com/app/docs) section on the PGP Support

https://support.pgp.com).

Contact Information

Contacting Technical Support

 To learn about PGP support options and how to contact PGP Technical

Support, please visit the PGP Corporation Support Home Page

https://support.pgp.com).

(

 To access the PGP Support Knowledge Base or request PGP Technical

Support, please visit PGP Support Portal Web Site (https://support.pgp.com). Note that you may access portions of the

PGP Support Knowledge Base without a support agreement; however, you must have a valid support agreement to request Technical Support.

 To access the PGP Support forums, please visit PGP Support

http://forum.pgp.com). These are user community support forums hosted

( by PGP Corporation.

Contacting Customer Service

 For help with orders, downloads, and licensing, please visit PGP

Corporation Customer Service (

https://pgp.custhelp.com/app/cshome).

Contacting Other Departments

 For any other contacts at PGP Corporation, please visit the PGP Contacts

Page (

http://www.pgp.com/about_pgp_corporation/contact/index.html).

 For general information about PGP Corporation, please visit the PGP Web

Site (

http://www.pgp.com).

PGP Desktop Basics

This section describes the PGP Desktop terminology and provides some high-level conceptual information on cryptography.

In This Chapter

PGP Desktop Terminology ........................................................................ 9

Conventional and Public Key Cryptography............................................. 12

Using PGP Desktop for the First Time .................................................... 13

PGP Desktop Terminology

To make the most of PGP Desktop, you should be familiar with the terms in the following sections.

PGP Product Components

PGP Desktop and its components are described in the following list. Depending on your license, you may not have all functionality available. For more information, see About PGP Desktop Licensing (on page

 PGP Desktop: A software tool that uses cryptography to protect your data

against unauthorized access. PGP Desktop is available for Mac OS X and Windows.

 PGP Messaging: A feature of PGP Desktop that automatically and

transparently supports all of your email clients through policies you control. PGP Desktop accomplishes this using a new proxy technology; the older plug-in technology is also available. PGP Messaging also protects many IM clients, such as AIM and iChat (both users must have PGP Messaging enabled).

 PGP Whole Disk Encryption: Whole Disk Encryption is a feature of

PGP Desktop that encrypts your entire hard drive or partition (on Windows systems), including your boot record, thus protecting all your files when you are not using them. You can use PGP Whole Disk Encryption and PGP Virtual Disk volumes on the same system. On Windows systems, you can protect whole disk encrypted drives with a passphrase or with a keypair on a USB token for added security.

5).

PGP® Desktop for Mac OS X PGP Desktop Basics

 PGP NetShare: A feature of PGP Desktop for Windows with which

you can securely and transparently share files and folders among selected individuals. PGP NetShare users can protect their files and folders simply by placing them within a folder that is designated as protected.

 PGP Keys: A feature of PGP Desktop that gives you complete control

over both your own PGP keys, and the keys of those persons with whom you are securely exchanging email messages.

 PGP Virtual Disk volumes: PGP Virtual Disk volumes are a feature of

PGP Desktop that let you use part of your hard drive space as an encrypted virtual disk. You can protect a PGP Virtual Disk volume with a key or a passphrase. You can even create additional users for a volume, so that people you authorize can also access the volume. The PGP Virtual Disk feature is especially useful on laptops, because if your computer is lost or stolen, the sensitive data stored on the PGP Virtual Disk is protected against unauthorized access.

 PGP Shred: A feature of PGP Desktop that lets you securely delete

data from your system. PGP Shred overwrites files so that even file recovery software cannot recover them.

 PGP Viewer: Use PGP Viewer decrypt, verify, and display

messages outside the mail stream

 PGP Zip: A feature of PGP Desktop that lets you put any combination

of files and folders into a single encrypted, compressed package for convenient transport or backup. You can encrypt a PGP Zip archive to a PGP key or to a passphrase.

 PGP Universal: A tool for enterprises to automatically and transparently

secure email messaging for their employees. If you are using PGP Desktop in a PGP Universal Server-managed environment, your messaging policies and other settings may be controlled by your organization’s PGP administrator.

 PGP Global Directory: A free, public keyserver hosted by PGP

Corporation. The PGP Global Directory provides quick and easy access to the universe of PGP keys. It uses next-generation keyserver technology that queries the email address on a key (to verify that the owner of the email address wants their key posted) and lets users manage their own keys. Using the PGP Global Directory significantly enhances your chances of finding a valid public key of someone to whom you want to send secured messages. PGP Desktop is designed to work closely with the PGP Global Directory.

Terms Used in PGP Desktop

Before you use PGP Desktop, you should be familiar with the following terms:

PGP® Desktop for Mac OS X PGP Desktop Basics

 Decrypting: The process of taking encrypted (scrambled) data and making

it meaningful again. When you receive data that has been encrypted by someone using your public key, you use your private key to decrypt the data.

 Encrypting: The process of scrambling data so that if an unauthorized

person gets access to it, they cannot do anything with it. The data is so scrambled, it’s meaningless.

 Signing: The process of applying a digital signature to data using your

private key. Because data signed by your private key can be verified only by your public key, the ability to verify signed data with your public key proves that your private key signed the data and thus proves the data is from you.

 Verifying: The process of proving that the private key was used to digitally

sign data by using that person’s public key. Because data signed by a private key can only be verified by the corresponding public key, the fact that a particular public key can verify signed data proves the signer was the holder of the private key.

 Keypair: A private key/public key combination. When you create a PGP

“key”, you are actually creating a keypair. As your keypair includes your name and your email address, in addition to your private and public keys, it might be more helpful to think of your keypair as your digital ID—it identifies you in the digital world as your driver’s license or passport identifies you in the physical world.

 Private key: The key you keep very, very private. Only your private key can

decrypt data that was encrypted using your public key. Also, only your private key can create a digital signature that your public key can verify.

Caution: Do not give your private key, or its passphrase, to anyone! And

keep your private key safe.

 Public key: The key you distribute to others so that they can send

protected messages to you (messages that can only be decrypted by your private key) and so they can verify your digital signature. Public keys are meant to be widely distributed.

Your public and private keys are mathematically related, but there’s no way to figure out your private key if someone has your public key.

 Keyserver: A repository for keys. Some companies host keyservers for the

public keys of their employees, so other employees can find their public keys and send them protected messages. The PGP Global Directory

https://keyserver.pgp.com) is a free, public keyserver hosted by PGP

( Corporation.

PGP® Desktop for Mac OS X PGP Desktop Basics

 Smart cards and tokens: Smart cards and tokens are portable devices on

which you can create your PGP keypair or copy your PGP keypair. Creating your PGP keypair on a smart card or token adds security by requiring possession of the smart card or token in order to encrypt, sign, decrypt, or verify. So even if an unauthorized person gains access to your computer, your encrypted data is secure because your PGP keypair is with you on your smart card or token. Copying your PGP keypair to a smart card or token is a good way to use it away from your main system, back it up, and distribute your public key. Smart cards and tokens are not available for key storage when used with PGP Desktop for Mac OS X.

Conventional and Public Key Cryptography

Conventional cryptography uses the same passphrase to encrypt and decrypt

data. Conventional cryptography is great for data that isn’t going anywhere (because it encrypts and decrypts quickly). However, conventional cryptography is not as well suited for situations where you need to send encrypted data to someone else, especially if you want to send encrypted data to someone you have never met.

Public-key cryptography uses two keys (called a keypair) for encrypting and decrypting. One of these two keys is your private key; and, like the name suggests, you need to keep it private. Very, very private. The other key is your public key, and, like its name suggests, you can share it with the general public. In fact, you’re supposed to share.

Public-key cryptography works this way: let’s say you and your cousin in another city want to exchange private messages. Both of you have PGP Desktop. First, you both need to create your keypair: one private key and one public key. Your private key you keep secret, your public key you send to a public keyserver like the PGP Global Directory (keyserver.pgp.com), which is a public facility for distributing public keys. (Some companies have their own private keyservers.)

Once the public keys are on the keyserver, you can go back to the keyserver and get your cousin’s public key, and she can go to the keyserver and get yours (there are other ways to exchange public keys; for more information, see Working with PGP Keys (on page encrypted email message that only your cousin can decrypt, you encrypt it using your cousin’s public key. What makes this work is that only your cousin’s private key can decrypt a message that was encrypted using her public key. Even you, who have her public key, cannot decrypt the message once it has been encrypted using her public key. Only the private key can decrypt data

that was encrypted with the corresponding public key.

Your public and private keys are mathematically related, but there’s no feasible way to figure out someone’s private key if you just have a public key.

43)). This is important because to send an

PGP® Desktop for Mac OS X PGP Desktop Basics

Using PGP Desktop for the First Time

PGP Corporation recommends the following procedure for getting started with PGP Desktop:

1 Install PGP Desktop on your computer.

If you are a corporate user, your PGP administrator may have specific installation instructions for you to follow or may have configured your PGP installer with certain settings. Either way, this is the first step.

2 Let the Setup Assistant be your guide.

To help you get started, after you install PGP Desktop and reboot your computer, the Setup Assistant is displayed. It assists with:

 Licensing PGP Desktop

 Creating a keypair—with or without subkeys (if you do not already

have a keypair).

 Publishing your public key on the PGP Global Directory.

 Enabling PGP Messaging

 Giving you a quick overview of other features.

If your PGP Desktop installer application was configured by a PGP administrator, the Setup Assistant may perform other tasks.

3 Exchange public keys with others.

After you have created a keypair, you can begin sending and receiving secure messages with other PGP Desktop users (once you have exchanged public keys with them). You can also use the PGP Desktop disk-protection features.

Exchanging public keys with others is an important first step. To send them secure messages, you need a copy of their public key, and to reply with a secure message, they need a copy of your public key. If you did not upload your public key to the PGP Global Directory using the Setup Assistant, do so now. If you do not have the public key for someone to whom you want to send messages, the PGP Global Directory is the first place to look. PGP Desktop does this for you—when you send email, it finds and verifies the keys of other PGP Desktop users automatically. It then encrypts your message to the recipient public key, and sends the message.

4 Validate the public keys you get from untrusted keyservers.

PGP® Desktop for Mac OS X PGP Desktop Basics

When you get a public key from an untrusted keyserver, try to make sure that it has not been tampered with, and that the key really belongs to the person it names. To do this, use PGP Desktop to compare the unique fingerprint on your copy of someone’s public key to the fingerprint on that person’s key (a good way to do that is by telephoning the key’s owner and having them read you the fingerprint information so that you can compare it). Keys from trusted keyservers like the PGP Global Directory have already been verified.

5 Start securing your email, files, and instant message (IM) sessions.

After you have generated your keypair and exchanged public keys, you can begin encrypting, decrypting, signing, and verifying email messages and files. The secure IM chat session feature generates its own keys automatically, so you can use this feature even before you generate your keypair. The only requirement is that you must be chatting with another PGP Desktop user for the chat session to be secured.

6 Watch for information boxes from the PGP Desktop Notifier feature to

appear.

As you send or receive messages, or perform other PGP Desktop functions, the PGP Desktop Notifier feature displays information boxes that appear in whichever corner of the screen you specify. These PGP Notifier boxes tell you the action that PGP Desktop took, or will take. After you grow familiar with the process of sending and receiving messages, you can change options for the PGP Notifier feature—or turn it off.

7 After you have sent or received some messages, check the logs to

make sure everything is working correctly.

If you want more information than the Notifier feature displays, the PGP Log provides detailed information about all messaging operations.

8 Modify your messaging policies, if necessary.

Email messages are sent and received—automatically and seamlessly—if PGP Desktop messaging policies are configured correctly. If your message recipient has a key on the PGP Global Directory the default PGP Desktop policies provide opportunistic encryption. Opportunistic encryption means that, if PGP Desktop has what it needs (such as the recipient's verified public key) to encrypt the message automatically, then it does so. Otherwise, it sends the message in clear text (unencrypted). The default PGP Desktop policies also provide optional forced encryption. This means that, if you include the text “[PGP]” in the Subject line of a message, then the message must be sent securely. If verified keys cannot be found, then the message is not sent, and a Notifier box alerts you.

9 Start using the other features in PGP Desktop.

Along with its messaging features, you can also use PGP Desktop to secure the disks that you work with:

PGP® Desktop for Mac OS X PGP Desktop Basics

 Use PGP Whole Disk Encryption to encrypt a boot disk, disk partition

(on Windows systems), external disk, or USB thumb drive. All files on the disk or partition are secured — encrypted and decrypted on the fly as you use them. The process is completely transparent to you.

 Use PGP Virtual Disk to create a secure “virtual hard disk.” You can

use this virtual disk like a bank vault for your files. Use PGP Desktop or Windows Explorer or the Mac OS X finder to unmount and lock the virtual disk, and your files are secure, even if the rest of your computer is unlocked.

 Use PGP Zip to create compressed and encrypted PGP Zip archives.

These archives offer an efficient way to transport or store files securely.

 Use PGP Shredder to delete sensitive files that you no longer need.

PGP Shredder removes them completely, eliminating any possibility of recovery.

Installing PGP Desktop

This section describes how to install PGP Desktop onto your computer and how to get started after installation.

In This Chapter

System Requirements............................................................................. 17

Installing and Configuring PGP Desktop.................................................. 17

Uninstalling PGP Desktop........................................................................ 22

Moving Your PGP Desktop Installation from One Computer to Another 23

System Requirements

The minimum system requirements to install PGP Desktop on your Mac OS X system are:

 Apple Mac OS X10.5.x or 10.6.x (Intel)

 512 MB of RAM

 64 MB hard disk space

Installing and Configuring PGP Desktop

This section includes information on installing or upgrading PGP Desktop, as well as information on the Setup Assistant.

Installing the Software

Note: You must have administrative rights on your system in order to install

the update.

The PGP Desktop installer walks you through the installation process.

PGP® Desktop for Mac OS X Installing PGP Desktop

 To install PGP Desktop on your Mac OS X system

1 Quit all other applications.

2 Mount the PGP DiskCopy image.

3 Double-click PGP.pkg.

4 Follow the on-screen instructions.

5 If prompted to do so, restart your system.

Note: If you are in a domain protected by a PGP Universal Server, your PGP

administrator may have preconfigured your PGP Desktop installer with specific features and/or settings. In addition, if your PGP administrator set up silent enrollment, your Windows domain password will be used for all passphrase requirements in PGP Desktop. If specified by policy, PGP Whole Disk Encryption may automatically start to encrypt your disk when your Windows password is entered.

Using PGP Desktop with Apple Boot Camp

Apple Boot Camp is compatible with PGP Desktop ver 10.0 or later. To use PGP Desktop with Boot Camp, you must install the software and encrypt the disk in a specific order.

Before you begin, be sure you have installed Boot Camp correctly. For information on how to set up Boot Camp, refer to the Boot Camp Installation and Setup Guide ( from Apple. Note that in order to use Windows XP in the Windows partition, you much configure the partition as FAT32. PGP Desktop does not support installing Linux on a partition in Boot Camp.

If you need to decrypt your disk, PGP Corporation recommends that you do so from the Mac OS X partition.

For more information on using PGP Desktop with Apple Boot Camp, see PGP KB Article 1697 (

Note: Be sure that your disk is not encrypted (if it is, decrypt the disk before

installing Boot Camp) and then uninstall PGP Desktop.

 To use Apple Boot Camp in a standalone environment

1 Install Apple Boot Camp.

2 Install PGP Desktop on the Mac OS X partition and complete installation

with the setup assistant.

http://manuals.info.apple.com/en/boot_camp_install-setup.pdf)

https://support.pgp.com/?faq=1697).

3 Boot into the Windows partition and install PGP Desktop on the Windows.

Do not run the setup assistant on the Windows partition.

PGP® Desktop for Mac OS X Installing PGP Desktop

4 Boot into the Mac OS X partition and encrypt your disk. At this point, if you

pause the encryption process while running Mac OS X, you can boot into the Windows partition but you must resume encryption while running Mac OS X.

 To use Apple Boot Camp in a PGP Universal Server-managed

environment

1 Install Apple Boot Camp.

2 Boot into the Windows partition and install PGP Desktop on the Windows.

Do not run the setup assistant on the Windows partition.

3 Install PGP Desktop on the Mac OS X partition and complete enrollment

with the setup assistant.

4 While still booted into the Mac OS X partition, begin to encrypt your disk.

At this point, if you pause the encryption process while running Mac OS X, you can boot into the Windows partition but you must resume encryption while running Mac OS X.

Upgrading the Software

Note: PGP Desktop for Mac OS X, and PGP Universal Satellite for Mac OS X

cannot both be installed in the same system. The installers for both products will detect the presence of the other program and end the install.

You can upgrade to PGP Desktop for Mac OS X from a previous version of one of the following products:

 PGP Desktop for Mac OS X

 PGP Universal Satellite for Mac OS X

Important Note: If you are upgrading your computer to a new version of the

operating system and want to use this version of PGP Desktop, be sure to uninstall any previous versions of PGP Desktop before upgrading the OS and installing this release. Be sure to back up your keys and keyrings before uninstalling. Note that if you have used PGP Whole Disk Encryption, you will need to unencrypt your disk before you can uninstall PGP Desktop.

Upgrading PGP Desktop

Do one of the following:

 From PGP Desktop 8.x or 9.x for Mac OS X, begin the installation

process for PGP Desktop 10.1 for Mac OS X.

PGP® Desktop for Mac OS X Installing PGP Desktop

The existing version of PGP Desktop for Mac OS X is automatically uninstalled, then PGP Desktop 10.1 for Mac OS X is installed. Existing keyrings and PGP Virtual Disk files are usable in the upgraded version.

 From a version of PGP Desktop for Mac OS X prior to Version 8.0, you

must manually uninstall the existing software before beginning the installation of PGP Desktop 10.1 for Mac OS X. Existing keyrings and PGP Virtual Disk files are usable in the upgraded version.

Upgrading from PGP Universal Satellite

Do one of the following:

 From PGP Universal Satellite version 1.2 or previous for Mac OS X,

begin the installation process for PGP Desktop 10.1 for Mac OS X.

Existing versions of PGP Universal Satellite for Mac OS X are automatically uninstalled, then PGP Desktop 10.1 for Mac OS X is installed. Existing settings are retained.

Caution: Installing any version of PGP Universal Satellite on top of PGP

Desktop 10.1 for Mac OS X is an unsupported configuration. Neither program will work correctly. Uninstall both programs and then reinstall only PGP Desktop.

Checking for Updates

 From PGP Desktop for Mac OS X (version 8.x) and PGP Universal

Satellite: Follow the installation process for PGP Desktop 10.1 for Mac OS

PGP Desktop for Mac OS X and PGP Universal Satellite for Mac OS X are both automatically uninstalled, then PGP Desktop 10.1 for Mac OS X is installed. Existing keyrings and PGP Virtual Disk files are usable in the upgraded version, as are existing PGP Universal Satellite for Mac OS X settings.

Note: The option to automatically check for updates is no longer available in

PGP Desktop, starting with version 10.1. To check for an update or to install an update, you must manually download the file.

With the acquisition of PGP Corporation by Symantec Corporation, PGP operations is in the process of integrating with Symantec operations. When checking to see if there are updates, or to download an update, use the second download link if the first link does not appear operational.

 To upgrade PGP Desktop, do the following:

 Go to the PGP License and Entitlement Management System (LEMS) and

https://lems.pgp.com/account/login). If the update for PGP Desktop

PGP® Desktop for Mac OS X Installing PGP Desktop

 Go to Symantec FileConnect (https://fileconnect.symantec.com/), select

your language, and enter your serial number.

Upgrading From Standalone to Managed PGP Desktop Installations

If you have been using PGP Desktop in standalone mode and now will be managed by a PGP Universal Server, you must install a bound and stamped version of PGP Desktop over your existing, standalone installation. You must also complete the enrollment process. Your PGP Administrator will provide an installation file so you can install a bound and stamped version.

Upgrading the Operating System Software

If you are upgrading your computer to a new major release of the operating system (for example, on a Windows system to Windows Vista or on a Mac OS X system from 10.4.x to 10.5.x), be sure to do the following:

1 Back up your keys and keyrings before uninstalling.

2 If you have used PGP Whole Disk Encryption, decrypt your disk before you

uninstall PGP Desktop.

3 Uninstall any previous versions of PGP Desktop before upgrading to the

new version of the operating system.

4 Once you have upgraded your version of the operating system, reinstall

PGP Desktop. Import your keys/keyring and, if necessary, you can then encrypt your disk.

Licensing PGP Desktop

For license information for this release, see the PGP Desktop Release Notes.

Running the Setup Assistant

The Setup Assistant displays a series of screens that ask you questions—then uses your answers to configure PGP Desktop for you.

If you have questions about any of the content on the Setup Assistant screens, click Help on the screen.

The Setup Assistant does not configure all PGP Desktop settings. When you finish going through the Setup Assistant screens, you can then configure those settings not covered in the Setup Assistant.

PGP® Desktop for Mac OS X Installing PGP Desktop

Integrating with Entourage 2008

The PGP Desktop for Mac OS X installation package includes scripts so you can integrate PGP Desktop with Entourage. Once the scripts are copied to the required folders, the Scripts menu in Entourage includes a PGP menu option. Use the Entourage scripts to encrypt email text without having to use an email proxy.

 To integrate PGP scripts with Entourage

1 If it is running, quit Entourage.

2 Open the PGP Desktop for Mac OS X download.

3 In the PGP Desktop download folder, open the Extras folder.

4 In the Extras folder, open the Entourage folder.

5 Double-click the file EntourageScripts.zip to extract the following

scripts from the zip file:

 Decrypt & Verify\mod

 Encrypt & Sign\moc

 Encript\moe

 Sign\mos

6 Copy and paste the scripts to the following folder:

 User Profile\Documents\Microsoft User Data\Entourage Script Menu

items\PGP

7 Start Entourage. The Scripts menu now includes a PGP menu option.

See Using PGP Scripts with Entourage 2008 (on page how to encrypt and decrypt messages.

Uninstalling PGP Desktop

 To uninstall PGP Desktop

1 In PGP Desktop, from the PGP menu, select Uninstall. A confirmation

dialog box is displayed.

2 Click Yes to continue with the uninstall process.

3 You are prompted to authenticate as the administrative user of the Mac OS

X system from which you are uninstalling PGP Desktop. Enter the appropriate password, then click OK. The PGP Desktop software is removed from your system.

119) for information on

PGP® Desktop for Mac OS X Installing PGP Desktop

Your keyring and PGP Virtual Disk files are not removed from your system, in case you decide to reinstall PGP Desktop in the future.

Moving Your PGP Desktop Installation from One Computer to Another

Moving a PGP Desktop installation from one computer to another is not a difficult process, although there are a few crucial steps which must be completed successfully. The process consists of the following steps:

 To transfer your PGP Desktop installation to another computer

1 Uninstall PGP Desktop. To do this, in PGP Desktop from the PGP menu,

select Uninstall.

Note that this step does not remove the keyring files.

2 Transfer the keyrings. To do this, copy the keyring files (both

pubring.pkr and secring.skr) from the old computer to removable media such as a flash drive, and then copy them to the new computer. The default location for the keyring files is in the PGP folder.

If PGP Desktop has never been installed on the new computer, create this folder first before copying the keyring files to the computer.

3 Install PGP Desktop on the new computer. To do this, download PGP

Desktop by clicking the download link in your original PGP order confirmation email.

4 During the installation process, do the following:

 During the PGP Desktop setup wizard on the new computer select

No, I have existing keyrings and specify the location where you

copied the keyring files to on the new computer.

 Use the same name, organization, and license number used when

PGP Desktop was originally authorized.

The PGP Desktop User

Accessing PGP Desktop Features

Interface

This section describes the PGP Desktop user interface.

In This Chapter

Accessing PGP Desktop Features........................................................... 25

PGP Desktop Notifier alerts..................................................................... 30

PGP Desktop and the Finder ................................................................... 35

Viewing the PGP Log............................................................................... 41

There are four main ways to access PGP Desktop:

 PGP Desktop Main Screen (on page 26)

 Using the PGP Desktop Icon in the Menu Bar (on page 27)

 Using the PGP Dock Icon (on page 28)

 Using the Mac OS X Finder (on page 29)

PGP® Desktop for Mac OS X The PGP Desktop User Interface

PGP Desktop Main Screen

The main screen of PGP Desktop is your primary interface to the product.

The PGP Desktop main screen includes:

The search field. Lets you search for keys on the local

keyring. Simply enter characters and the names and email addresses on the local keyring that include those characters will display. Click Advanced Search for more search criteria.

The PGP Desktop Work area. Displays information

about and actions you can take for the selected item.

The Toolbar. Provides access to frequently used

features. You can:

Create a new PGP Zip archive.

Create a new PGP Virtual Disk.

Mount an existing PGP Virtual Disk.

Synchronize keys.

Shred files.

The Keys item. Gives you control over the PGP keys

that PGP Desktop is managing for you.

The PGP Disk item. Use this item to view and manage

PGP Virtual Disk volumes. Also, you can use this item to create new PGP Virtual Disk volumes, as well as encrypting an entire non-boot disk using the PGP Whole

PGP® Desktop for Mac OS X The PGP Desktop User Interface

Disk Encryption feature.

The PGP Messaging item. Use this item to manage

PGP Messaging services. You can also use this item to create new services and policies, and manage existing services and policies.

The Keyservers item. Use this item to view and

manage keyservers.

( not shown) The PGP Zip item. Use this item to view and manage PGP Zip archives.

Using the PGP Desktop Icon in the Menu Bar

One way to access many PGP Desktop features is from the PGP Desktop icon in the Menu Bar.

When you click the PGP Desktop icon in the Menu Bar, the PGP menu is displayed. Note that not all options may be available, depending on if you are a standalone or managed installation.

 About PGP Desktop. Displays a window with information about the

version of PGP Desktop you are using, licensing information, and a list of the people who helped create PGP Desktop. This window also has a button that you can use to uninstall PGP Desktop.

 Help. Opens the PGP Desktop integrated online help.

 Open PGP Desktop. Opens the PGP Desktop main screen.

 Open PGP Viewer. Opens PGP Viewer so you can decrypt email out of the

mail stream.

 View Notifier. Displays the PGP Desktop Notifier box, so you can review

the Notifier messages that have appeared.

 Show Log. Displays the PGP Desktop Log. Use the PGP Desktop Log to

see what actions PGP Desktop is taking to secure your data.

 Clear Log. Clears the PGP Log.

 Update Policy. Manually downloads policy from the PGP Universal Server.

This option is available only for managed installations.

 Change Passphrase. Provides a shortcut so you can change your

passphrase on your key. This option is available only for managed installations.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

 Purge Caches. Clears from memory any cached information, such as

passphrases and cached public keys.

 Hide. Removes the PGP icon from the menu bar, but leaves the

background parts of the application running.

The Hide command becomes the Quit command if you hold down the

Option key before clicking the PGP Desktop icon. This removes the PGP

Desktop icon from the menu bar and causes the background parts of PGP Desktop to quit. Shortcut menu functionality continues to work.

Caution: If you use the Option key and the PGP Menu Bar icon to quit the

background parts of PGP Desktop, email messages are no longer encrypted, decrypted, signed, or verified. You may also not be able to decrypt messages received while the background parts of PGP Desktop were not running, even after they are started again. Finally, no key management is done while the background parts of the software is not running. For these reasons, it is recommended that you keep the PGP Desktop background processes running at all times.

 To restart the background processes of PGP Desktop if the application is

not running

1 Locate the PGP Desktop application on your system. The default location is

in the Applications folder.

2 Double-click the PGP Desktop application icon. PGP Desktop starts and its

icon is displayed in the Menu Bar.

Using the PGP Dock Icon

One way to access many PGP Desktop features is from the PGP Dock icon.

Use the PGP Desktop icon in the Mac OS X Dock in any of these ways, then select an option from the menu displayed:

 Click the PGP Desktop Dock icon and hold the mouse button down.

 Ctrl+click the Dock icon.

 Right-click the Dock icon, if you are using a two-button mouse.

The PGP Desktop icon is displayed in the Dock when the application is open, or when you have put the PGP Desktop icon into the Dock manually.

When you click and hold the PGP Desktop icon in the Dock when the application is already open (or Ctrl+click it, or use the right mouse button if you are using a two-button mouse), a menu is displayed giving you access to the following commands:

PGP® Desktop for Mac OS X The PGP Desktop User Interface

 Any currently-open PGP Desktop windows. If PGP Desktop is currently

running, any of its windows that you have open appear at the top of this menu.

 About PGP Desktop. Displays the PGP Desktop About dialog box. The

About dialog box displays the PGP Desktop credits, what version you are currently using, and has a button that you can use to uninstall the PGP Desktop software.

 Preferences. Opens the PGP Desktop Preferences.

 Clipboard. Lets you Encrypt, Sign, Encrypt & Sign, or Decrypt/Verify the

contents of the Clipboard.

 Purge Caches. Clears from memory any cached information, such as

passphrases and cached public keys.

The remaining menu items, in the lowest section of the menu, are standard Mac OS X Dock items:

 Remove from Dock/Keep in Dock. Removes or adds the PGP Desktop

icon in the Dock.

 Open at Login. Sets your Mac OS X Account System Preference so that

PGP Desktop starts when you log on to your computer.

 Show In Finder. Shows the location of the PGP Desktop application in a

Finder window.

 Hide. Hides any PGP Desktop application screens.

 Quit. Quits the PGP Desktop application.

If you click and hold the PGP Desktop icon in the Dock when the application is not open, you see the standard Mac OS X Dock items.

Using the Mac OS X Finder

From the Desktop or a Finder window, Ctrl+click a file or folder (or right-click it if you have two-button mouse) then select PGP from the shortcut menu displayed.

You can also access PGP Desktop functions from the Mac OS X Finder.

 To use the Mac OS X Finder

1 Open a Finder window.

2 Ctrl+click (or right-click, if you are using a two-button mouse) the desired

file or folder.

3 Select the appropriate option from the PGP shortcut menu. Choose

Encrypt, Sign, Encrypt & Sign, Decrypt/Verify, Shred, or Mount (if you

have PGP Virtual Disks).

Tip: You can also right-click a file or folder from the Desktop.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

PGP Desktop Notifier alerts

The PGP Desktop Notifier feature displays a small information box that tells you the status of incoming and outgoing email messages, as well as instant messaging sessions.

In a PGP Universal Server-managed environment, your administrator may have specified certain notifications settings (for example, whether notifications are to be displayed or the location of the notifier). In this case, you may not see any notifier messages at all.

PGP Desktop Notifier for Messaging

Use the PGP Desktop Notifier for Messaging feature to:

 See if an incoming email is properly decrypted and/or signed.

 See if an outgoing email is properly encrypted and/or signed.

 Stop an email message from being sent if the encryption options are not

what you want.

 View a quick summary of the sender, subject, and encryption key of an

email.

 Review, at any time, the status of previous incoming or outgoing messages

for that Windows session.

 See that a chat session with another PGP Desktop user is being secured.

Use the PGP Desktop Notifier feature to monitor all or some of your incoming email, as well as maintain precise control over all or some of your outgoing messages. The choice is yours. You can set various Notifier options, or turn the PGP Desktop Notifier feature completely off if you prefer.

Some additional points about the PGP Desktop Notifier feature:

 For message notifications, use the left and right arrow buttons in the

upper-right corner of the Notifier box to scroll Notifier messages forward or backward. This way, you can review messages that came before or after the message you are viewing currently.

 When they first display, Notifier message boxes have a partially transparent

appearance to prevent obscuring anything on your screen. Notifier message boxes become opaque if you move your cursor over them, and become translucent again when you move your cursor away from them.

 Unless the cursor is over them, Notifier messages display for four seconds

(this default setting can be changed in the Notifier options). If you want more time to read a Notifier, move your cursor over the Notifier and it remains on your display.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

 If you completely miss reading a Notifier, or you would like to review

previous ones, do the following:

 On Windows systems, choose View Notifier from the PGP Tray icon.

 On Mac OS X systems, choose View Notifier from the PGP Desktop

icon in the Mac OS X Menu Bar.

 Close a Notifier message by clicking the X (in the upper right corner of the

message on Windows systems, in the upper left corner on Mac OS X systems).

For more information about setting PGP Desktop Notifier options, see Notifier Options (see "Notifications Preferences" on page 198).

Incoming PGP Desktop Notifier messages

Notifications for incoming email provide information on whether the email was decrypted and verified, or decrypted and signed by an unverified or unknown key.

Outgoing PGP Desktop Notifier messages

For simple notification, choose to have a PGP Desktop Notifier appear momentarily when email is sent (all email, or email meeting certain criteria). The notifier message displays information that PGP Desktop is searching for the public keys of the person in the To line. When the appropriate keys are found, the Status line changes to indicate the message will be sent encrypted. If the appropriate keys cannot be found, PGP Desktop follows policy and may send the message unencrypted or block the message.

After a message has been sent encrypted, click More to see the details of how PGP Desktop handled the message. It is not necessary for you to view this additional information unless you want to see it. To hide the additional information again, click Less.

You can delay a message from being sent by moving your cursor over the Notifier box. If you do not do this within 4 seconds (you can set this interval in preferences for the Notifier feature) the message is sent unencrypted, and the Status field reflects that.

If you do move your cursor over the message, Block and Send buttons appear in the Notifier box. Click Block to stop the message from being transmitted, or

Send to send the message.

If you send an email to more than one recipient, and PGP Desktop is able to find keys for some recipients but not others, the Notifier informs you of the status, and gives you two options:

 Send the email encrypted to those with keys, and unencrypted to those

without them.

 Block the message so it is sent to no one.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

Outgoing PGP Desktop Notifier Messages for Offline Policy

If you are using PGP Desktop in a PGP Universal Server-managed environment, your administrator may have specified what actions to take on outgoing messages if the PGP Universal Server is not available. The outgoing notifier message indicates one of the following:

 Your PGP Universal Server is not available and policy has been set to block

all messages. Email messages remain in your outbox and are sent when the PGP Universal Server can be contacted.

 Your PGP Universal Server is not available and policy has been set to send

all messages in the clear.

 Your PGP Universal Server is not available and policy has been set to allow

your local policy to take precedence.

In the latter two cases, you can choose to send or block the outgoing message as you would any other outgoing message.

PGP Notifier for Instant Messaging

If you have PGP Desktop installed on your computer, and if you have specified to receive Notifiers for Instant Messaging (under the Notifications tab in PGP Desktop Preferences), then PGP Desktop Notifiers alert you when the AOL Instant Messenger (AIM) sessions that you have with other PGP Desktop users are protected.

When you use the secure instant messaging feature, a Notifier displays when you log on to the instant messaging program to inform you that your chat is secure, and a padlock icon displays next to your “buddy name” with most AIM-compliant instant messaging clients.

When you log off of your instant messaging program, a final Notifier message informs you that the secure session has ended.

For more information on proper configuration, as well as the use of the secure instant message chat feature, see Securing Instant Messages.

Enabling or Disabling Notifers

 To enable or disable Notifiers

1 Open PGP Desktop and select PGP > Preferences.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

2 Click the Notifier icon.

3 Under Usage, specify if you want to Use PGP Notifer and, if so, the

location. PGP Desktop Notifications can appear at any of the four corners of your screen (Lower Right, Lower Left, Upper Right, or Upper Left). Select the corner that you want PGP Desktop Notifications to appear. The default position is Upper Left.

4 If you are using PGP Desktop Messaging and you want PGP Desktop

Notifiers to appear, informing you of encryption and/or signing status when you send email, select the checkbox to Notify when processing

outbound email. Deselect this checkbox to stop PGP Desktop Notifiers

from appearing when you send mail.

5 PGP Desktop looks for a public key for every recipient of the email

messages that you send. By default, if it cannot find a public key for a recipient, it sends that email in the clear (without encryption). Select Ask

me before sending email when the recipient’s key is not found if you

want to be notified when a key is not found and be given a chance to block the email so that it is not sent. Then specify the following options:

 Always ask me before sending email: Select this checkbox if you

would prefer approving every email that you send. You can review the encryption status in the Notifier, and either send or block the email.

 Delay outbound email for n second(s) to confirm (where n is a

number from 1-30; the default is 4 seconds). To change the amount of time that outbound messages are delayed, and a PGP Desktop Notifier is displayed, click the up or down arrows. Use the delay period to review the PGP Desktop Notifier message.

(For more information on the PGP Desktop default policy settings, see Services and Policies (on page

90).)

6 For incoming email, specify how you are notified of its status upon arrival.

Select one of the following for Display notifications for incoming mail:

 When receiving secured email—A Notifier appears whenever you

receive secured email. The box displays who the email is from, its subject, its encryption and verification status, and the email address of the person sending it.

 Only when message verification fails—For incoming email, you see

a Notifier only when PGP Desktop is unable to verify the signature of the incoming email.

 Never—If you do not need or want to see a Notifier as you receive

email, select this option. This option does not affect Notifiers for outgoing mail.

7 If you want a PGP Desktop Notifier to appear briefly when you begin a

secure instant message chat, and appear briefly again when the chat ends, select the checkbox to Notify for status of PGP Encrypted IM sessions.

PGP Desktop and the Finder

This section describes how you can access certain PGP Desktop functions using shortcut menus in the Finder.

In This Chapter

Overview ................................................................................................. 35

Encrypt, Sign, or Encrypt and Sign .......................................................... 36

Shred ....................................................................................................... 37

Decrypt/Verify .......................................................................................... 38

Mount or Unmount a PGP Virtual Disk Volume....................................... 39

Import a PGP Key .................................................................................... 39

Add PGP Public Keys to Your Keyring ..................................................... 40

Extract the Contents of a PGP Zip Archive.............................................. 40

Overview

Access PGP Desktop functions using shortcut menus in the Finder to get the same PGP Desktop functionality from the Mac OS X Services menu.

Depending on what you select, you can:

 Encrypt, Sign, or Encrypt and Sign

 Shred

 Decrypt/verify

 Mount, edit, or unmount a PGP Virtual Disk volume

 Import a PGP key

 Add PGP keys to your keyring

View the contents of a PGP Zip archive Access shortcut menus in the Finder by:

 Ctrl+clicking: With a one-button mouse, hold down the Control (ctrl) key on

the keyboard and click the item.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

 Right-clicking: On a two-button mouse, click the item with the right mouse

button held down.

In this document, the Ctrl+click method is used. If you right-click or use a different method for accessing shortcut menus in the Finder, substitute that method where it says to Ctrl+click.

Note: Files “in the Finder” also include files on the Mac OS X Desktop.

Encrypt, Sign, or Encrypt and Sign

PGP Desktop lets you encrypt, sign, or encrypt and sign unencrypted files, folders, and even entire drives from the Finder.

Encrypting and/or signing files and folders is a good way to protect just a few important files and/or folders in a situation where a PGP Virtual Disk volume is not justified.

If you are considering encrypting and/or signing a drive in the Finder, a PGP Virtual Disk volume might be a better solution. For more information, see Using PGP Virtual Disks.

 To encrypt and/or sign files and/or folders in the Finder

1 In the Finder, select the files and/or folders you want to encrypt and/or

sign. Use the Shift or Command keys to select any combination of files and folders.

2 Ctrl+click the selected files and/or folders, or right-click if you have a

two-button mouse. From the shortcut menu, choose Encrypt & Sign from the PGP menu. (If you select just Encrypt, you will not be prompted for a signing key; if you select just Sign, you will not be prompted to select a public key to encrypt to.) The PGP Recipients dialog box is displayed.

3 Drag the public keys of the persons you want to be able to decrypt the

items you are encrypting into the Recipients field at the bottom of the dialog box.

4 Click the down arrow icon above the OK button to specify the appropriate

options:

 Conventional Encrypt. Select this checkbox to rely on a common

passphrase rather than on public-key cryptography. The file is encrypted using a session key, which encrypts (and decrypts) using a passphrase you specify.

If you are using PGP Desktop in a PGP Universal Server-managed environment, conventional encryption may be disabled.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

 Text Output. When sending files as attachments with some email

applications, you may need to select the Text Output checkbox to save the file as ASCII text. This is sometimes necessary in order to send a binary file using older email applications. Selecting this option increases the size of the encrypted file by about 30 percent.

 Shred Original. Select this checkbox to overwrite the original

document that you are encrypting, so that your sensitive information is not readable by anyone who can access your system.

 MacBinary. MacBinary is the standard method by which a Mac OS X

file is converted into a single file so that it can be transferred to another Macintosh or PC without losing either its Data or Resource segment. Options are Yes, No, or Smart.

Yes means the whole file is included, including the Mac OS X specific

information. No means only the data segment is included. Smart means the file type determines if the Mac OS X specific information is included.

5 Click OK. If you selected the Conventional Encryption option, you are

prompted for a passphrase to protect the encrypted items.

Shred

6 Enter a passphrase, enter it again, then click OK. The Enter PGP

Passphrase dialog box is displayed.

7 Using the Signing Key list, specify a private key to be used to sign the

items you are encrypting and signing, then enter the passphrase of the signing key. If the passphrase is cached, you do not have to enter it.

Normally, as an added level of security, the characters you enter for the passphrase do not appear on the screen. However, if you are sure that no one is watching (either physically or over the network) and you would like to see the characters of your passphrase as you type, select the Show

Keystrokes checkbox.

8 To save your passphrase in the Mac OS X Keychain, select the box. You

will not need to enter the passphrase the next time you access this feature.

9 Click OK. A PGP Zip archive (<file name>.pgp) file is created at the same

location as the encrypted and signed items.

For those situations where you want to be absolutely certain that specific files and/or folders are securely deleted from your system, you can Shred them from the Finder.

Putting a file or folder into the Mac OS X Trash just allows new files to overwrite the file or folder you think you are “deleting.” In fact, there could be days, weeks, or even months when just about anyone with physical access your system could retrieve these files.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

The PGP Desktop Shred feature, in comparison, overwrites your files multiple times as soon as you ask them to be shredded. For more information about how thoroughly the Shred feature erases your files, see Shredding Files.

 To Shred files and/or folders in the Finder

1 In the Finder, select the files and/or folders you want to Shred. Use the

Shift or Command keys to select any combination of files and folders.

2 Ctrl+click the selected files and/or folders, or right-click if you are using a

two-button mouse.

3 Choose PGP, then Shred from the shortcut menu. A PGP screen is

displayed, asking if you are sure you want to Shred the listed files.

4 Click OK. The file(s) are Shredded (secure deleted) from your system; they

do not appear in the Trash.

Decrypt/Verify

If you have a PGP Zip (.pgp) file on your system, you can decrypt and verify it in the Finder. Decrypt/verify will always decrypt an encrypted (.pgp) file. However, if the encrypted file was not signed, then the file will not be verified (as there’s no signature to verify).

You can also decrypt/verify a PGP key (.asc) file, but this is just for importing the keys, not for decrypting or verifying the file. For more information about importing PGP keys from a .asc file in the Finder, see Import a PGP Key (on

39).

page

 To decrypt/verify a PGP Zip file in the Finder

1 In the Finder, select the PGP Zip (.pgp) file you want to decrypt/verify.

2 Ctrl+click the selected files and/or folders, or right-click if you are using a

two-button mouse. Choose PGP, then Decrypt & Verify from the shortcut menu. The Enter PGP Passphrase dialog box is displayed.

3 Enter the appropriate passphrase for the private key. If the passphrase is

cached, you aren’t prompted for it.

Keystrokes checkbox.

4 To save your passphrase in the Mac OS X Keychain, select the box. You

will not need to enter the passphrase the next time you access this feature.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

5 Click OK. The file is decrypted at the location of the .pgp file. If the file

was signed, PGP Desktop opens the Verification Info window and displays the results of the verification of the file.

Mount or Unmount a PGP Virtual Disk Volume

If you have an unmounted PGP Virtual Disk (.pgd) file, you can mount the corresponding PGP Virtual Disk volume from the Finder. For more information about PGP Virtual Disk volumes, see Using PGP Virtual Disks.

 To mount a PGP Virtual Disk volume from the Finder

1 In the Finder select the PGP Disk (.pgd) file for the volume you want to

mount. Ctrl+click the selected .pgd file, or right-click if you are using a two button mouse. From the PGP menu, select Mount. The Enter PGP Passphrase dialog box is displayed.

2 Enter the passphrase that protects the PGP Disk volume you want to

mount.

Import a PGP Key

3 Click OK. The PGP Disk volume is mounted.

 To unmount a PGP Virtual Disk volume in the Finder

1 Select the mounted PGP Disk (.pgd) file for the volume you want to

unmount.

2 Ctrl+click the .pgd file, or right-click if you are using a two-button mouse.

From the shortcut menu, choose Unmount from the PGP menu. The selected PGP Disk volume is unmounted.

Tip: If the menu says Mount, then the volume is already unmounted.

PGP keys can be exported from PGP Desktop as .asc files. This is a good way to back up your keys or exchange your public keys with others. If you have an .asc file on your system that includes a PGP key that you want on your keyring, you can import it from the Finder.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

 To import keys from an .asc file in the Finder

1 In the Finder, locate the PGP key (.asc) file with the PGP keys you want to

import.

2 Double-click the selected .asc file. PGP Desktop opens and the Select

Keys dialog box is displayed.

3 Select the PGP key(s) you want to import, then click OK. The selected

key(s) are added to your keyring.

Tip: You can also import a key by selecting File > Open and browsing to the

desired .asc file.

Add PGP Public Keys to Your Keyring

PGP Desktop stores your PGP keys on keyrings; you always have one private keyring (.skr) file that holds private keys and one public keyring (.pkr) file that holds public keys.

If you have a public keyring file (not your active public keyring file) on your system that holds keys you would like to add to your active keyring, you can add them from the Finder.

 To add PGP public keys from a keyring file in the Finder

1 In the Finder, drag the PGP public keyring (.pkr) or PGP private keyring

(.skr) file and drop it onto your active keyring in the PGP DT window. The Select Keys dialog box opens and displays the public keys on the selected public keyring file.

2 Select the keys you want to add to your active keyring, then click OK. You

can use Select All or Select None and the Shift and Command keys to select the desired keys. The Select Keys dialog disappears and the selected keys are added to your active keyring.

Tip: In the Finder, double-click the PGP public keyring (.pkr) or PGP private

keyring (.skr) file. The new keyring will appear in PGP Desktop, below your existing keyrings, as "PGP Public Keyring."

Extract the Contents of a PGP Zip Archive

If you have a PGP Zip archive on your system whose contents you want to extract, you can do that in the Finder.

 To extract the contents of a PGP Zip archive in the Finder

1 In the Finder, select the PGP Zip archive (.pgp) file whose contents you

want to extract.

PGP® Desktop for Mac OS X The PGP Desktop User Interface

2 Ctrl+click the .pgp file, or right-click if you are using a two-button mouse.

From the shortcut menu, choose Decrypt & Verify from the PGP menu. The Enter PGP Passphrase dialog box is displayed.

3 Enter the passphrase that protects the PGP Zip archive from which you are

extracting files, then click OK. The file(s) are extracted from the archive to the same location in the Finder as the archive.

4 If the archive was signed, the Verification Info dialog is displayed.

Viewing the PGP Log

Use the PGP Log to see what actions PGP Desktop is taking to secure your data. For more information, see Viewing the PGP Log (on page 118).

Working with PGP Keys

PGP Keys is the feature of PGP Desktop you use to create and maintain your keypair(s) and the public keys of other PGP Desktop users.

This section describes viewing keys, creating a keypair, distributing your public key, getting the public keys of others, and working with keyservers.

Note: If you are using PGP Desktop in a PGP Universal Server-managed

environment, your PGP Universal Server administrator may have disabled certain features. When a feature is disabled, the control item in the left side is not displayed and the menu and other options for that feature are not available. The graphics included in this guide depict the default installation with all features enabled. If your PGP Universal Server administrator has disabled this functionality, this section does not apply to you.

In This Chapter

Viewing Keys ........................................................................................... 44

Creating a Keypair.................................................................................... 46

Protecting Your Private Key..................................................................... 49

Distributing Your Public Key .................................................................... 51

Getting the Public Keys of Others........................................................... 54

Working with Keyservers ........................................................................ 56

Using Master Keys .................................................................................. 57

PGP® Desktop for Mac OS X Working with PGP Keys

Viewing Keys

To view all of the keys on the local keyring, open PGP Desktop and click the

Keys item.

You can also use the Smart Keyrings feature. A Smart Keyring is a set of keys that fits the criteria you establish. For example, if you frequently send messages to PGP Desktop users from a particular email domain, you could create a Smart Keying that shows just the users from that email domain. The default Smart Keyring is My Private Keys.

Some of the more common tasks you may want to perform are available from the PGP Keys work area. These are:

 Send an email to the owner of a public key. To do this, Ctrl+click (or

right-click) a public key in any view of the PGP Keys on your keyrings and select Send Email.

 If you perform a search, and you select a public key found in the search

that is not on your local keyrings, add the key to your keyring. To do this, Ctrl+click (or right-click) the key and select Add to Default Keyring.

 To see the properties of any key displayed in the work area, double-click

any part of the key listing to display the Key Info dialog box for that key.

PGP® Desktop for Mac OS X Working with PGP Keys

Creating a Smart Keyring

 To create a Smart Keyring

1 Open PGP Desktop.

2 Click the Keys item.

3 Select File > New > Smart Keyring. The New Smart Keyring dialog box is

displayed.

4 In the Smart Keyring name field, enter a descriptive name for the Smart

Keyring you are creating.

5 In the Include keys which match the following conditions menu, select

either:

 Any. Displays keys that match any of the specified criteria (logical

“OR”).

 All. Only displays keys that match all of the specified criteria (logical

“AND”).

6 In the first matching column, select one of the following:

 Key is. Displays keys that meet the criteria.

 Key is not. Displays keys that do not meet the criteria.

 Name. Displays keys with the specified criteria in the Name.

 Email. Displays keys with the specified criteria in the Email address.

 Key ID. Displays keys with the specified criteria in the Key ID.

 Key Size. Displays keys of the specified Key Size.

 Creation Date. Displays keys created on the specified Creation Date.

 Expiration Date. Displays keys that expire on the specified Expiration

Date.

7 The options in the second matching column change based on what you

selected in the first matching column; select between:

 Public. Matches on public keys only.

 Private. Matches on private keys only.

 Revoked. Matches on revoked keys only.

 Enabled. Matches on enabled keys only.

 Expired. Matches on expired keys only.

 Signed by. Matches on keys signed by the specified person.

 Contains. Matches when key contains specified criteria.

PGP® Desktop for Mac OS X Working with PGP Keys

 Does not contain. Matches when key does not contain specified

criteria.

 Is. Matches when specified criteria (name or date) is met.

 Is not. Matches when specified criteria is not met.

 Is at least. Matches when specified criteria is at least the key size

entered.

 Is at most. Matches when specified criteria is no great than the key

size entered.

 Is on or before. Matches when specified date is on or before the

listed date.

 Is on or after. Matches when specified data is on or after the listed

date.

8 In the text box that is available for some matching items, you can enter text

(such as an email address or a domain; wildcards are allowed), numbers, or dates.

9 To add extra rows for matching or excluding, click the plus sign icon. Click

the minus sign icon to remove rows.

10 Click Save. The Smart Keyring is displayed in the Items list.

When you select this Smart Keyring, only those keys that match these criteria are listed. The following Smart Keyring, for example, matches the public keys of PGP Desktop users at your company’s law firm.

Creating a Keypair

You probably already created a PGP keypair for yourself using the PGP Desktop Setup Assistant or with a previous version of PGP Desktop — but if you have not, you need to now. Most of the things you do with PGP Desktop require a keypair.

Caution: It is bad practice to keep creating new keys for yourself. A PGP

keypair is like a digital driver’s license or passport; if you create lots of them, you’re going to end up confusing yourself and those people who want to send you encrypted messages. It is best to have only one key that contains all the email addresses that you use. The PGP Global Directory will publish only one key per email address.

If you are using PGP Desktop in a PGP Universal Server-managed environment, keypair creation may be disabled.

 To create a PGP keypair

1 Open PGP Desktop.

PGP® Desktop for Mac OS X Working with PGP Keys

2 From the File menu, select New > PGP Key. The Create a key to secure

your communications dialog box is displayed. Information on this dialog box explains what a key pair is and how it is used.

3 To specify advanced properties for your new key, select the Expert Mode

check box. For more information on these settings, see Expert Mode Key Settings (on page

48). Skip this step if you do not want to use Expert

Mode.

4 Click Continue. The Set your key’s contact information dialog box is

displayed.

5 Enter your real name in the Full Name field and your correct email address

in the Email Address field.

Note: It is not absolutely necessary to enter your real name or even your

email address. However, using your real name makes it easier for others to identify you as the owner of your public key. Also, when you upload your public key to the PGP Global Directory (which makes it easily available to other PGP Desktop users), your real email address is required.

6 Click Continue. The Set your key’s passphrase dialog box is displayed.

7 Enter a passphrase for the key you are creating, then enter it again to

confirm it.

Normally, as an added level of security, the characters you enter for the passphrase do not appear on the screen. However, if you are sure that no one is watching, and you would like to see the characters of your passphrase as you type, click Show Keystrokes.

Caution: Make sure that your passphrase is one that you can easily

remember (without writing it down). Unless your PGP administrator has implemented a PGP key reconstruction policy for your company, no one, including PGP Corporation, can salvage a key with a forgotten passphrase.

The Passphrase Quality bar provides a basic guideline for the strength of the passphrase you are creating by comparing the amount of entropy in the passphrase you type against a true 128-bit random string (the same amount of entropy in an AES128 key). For more information, see The Passphrase Quality Bar (on page

202).

8 To save this passphrase in the Mac OS X Keychain, select the check box.

9 Click Continue. The PGP Key creation summary dialog box is displayed.

10 If desired, do the following:

 To show details about the key, select Show Details.

 To make any changes to your key, click Go Back.

11 Click Create Key. PGP Desktop generates your new keypair. This process

can take several minutes.

12 When the key generation process indicates that it is complete, click Finish.

PGP® Desktop for Mac OS X Working with PGP Keys

Expert Mode Key Settings

1 When you select Expert Mode on the New PGP Key dialog box, in addition

to specifying your name and email address, you also specify:

 Key Type. Choose between Diffie-Hellman/DSS and RSA.

Note: Beginning with PGP Desktop 9.0, the older RSA Legacy key format

from the early 1990s is no longer fully supported. You cannot create new PGP keypairs using the RSA Legacy key format; however, existing RSA Legacy keypairs continue to be supported in PGP Desktop.

 Keyserver. Specify a trusted keyserver or <None>.

 Allowed Compression. Deselect any compression type you do not

want the key you are creating to support.

 Allowed Ciphers. Deselect any cipher you do not want the key you

are creating to support.

 Allowed Hashes. Deselect any hash you do not want the keypair you

are creating to support.

 Preferred Cipher. Select the cipher you want to be used in those

cases where no cipher is specified. Only a cipher that is allowed can be selected as preferred.

 Preferred Hash. Select the hash you want to be used in those cases

where no hash is specified. Only a hash that is allowed can be selected as preferred.

 Key size. Enter from 1024 bits to 4096 bits. The larger the key, the

more secure it is, but the longer it will take to generate.

 Key Expires. Select Never or specify a date on which the key you are

creating will expire.

2 Click Continue. The Set Your Key’s Passphrase dialog box is displayed.

3 Enter the passphrase that you would like to use with this key, then type it

again in the Confirm your passphrase field. It is critical that you keep this passphrase secret.

4 Click Continue.

5 Review the summary information, then click Create Key to begin the key

generation process. PGP Desktop generates your new keypair.

This process can take several minutes.

6 When the key generation process indicates that it is done, click Next. You

are prompted to add the public key portion of the key you just created to the PGP Global Directory.

7 Read the text on the screen and click Next.

PGP® Desktop for Mac OS X Working with PGP Keys

8 Click Skip to prevent the public key from being posted to the PGP Global

Directory. The Completing the PGP Global Directory Assistant screen is displayed.

9 Click Finish. Your new PGP keypair has been generated. It should be

visible in the PGP Keys Work area. If you don’t see it listed, make sure All

Keys or My Private Keys is selected in the PGP Keys item.

Protecting Your Private Key

PGP Corporation recommends that you take these actions immediately after you create your keypair:

Caution: Failure to take these actions could result in a devastating loss of

data some time in the future.

 Back up a copy of your private key file to another, safe location, in case

your primary copy is ever damaged or lost. See Backing up Your Private Key (on page 50).

 Reflect on your chosen passphrase to ensure that you chose something

that you will not forget. If you are concerned that you chose a passphrase during the key creation process that you will not remember, change it RIGHT NOW to something you will not forget. For information on changing your passphrase, see Changing Your Passphrase (on page

Your private key file is very important because once you have encrypted data to your public key; only the corresponding private key can be used to decrypt the data. This holds true for your passphrase as well; losing your private key or the passphrase means that you will not be able to decrypt data encrypted to the corresponding public key. When you encrypt information, it is encrypted to both your passphrase and your private key. You need both to decrypt the encrypted data. Once the data is encrypted, no one—not even PGP Corporation—can decrypt the data without your private key file and your passphrase.

Consider a situation where you have important encrypted data, and then either forget your passphrase or lose your private key. The encrypted data would be inaccessible, unusable, and unrecoverable.

Protecting Keys and Keyrings

Besides making backup copies of your keys, you should be especially careful about where you store your private key. Even though your private key is protected by a passphrase that only you should know, it is possible that someone could discover your passphrase and then use your private key to decipher your email or forge your digital signature. For instance, somebody could look over your shoulder and watch the keystrokes you enter or intercept them on the network or even over the Internet.

63, on page 63).

PGP® Desktop for Mac OS X Working with PGP Keys

To prevent anyone who might happen to intercept your passphrase from using your private key, store your private key only on your own computer. If your computer is attached to a network, make sure that your files are not automatically included in a system-wide backup where others might gain access to your private key. Given the ease with which computers are accessible over networks, if you are working with extremely sensitive information, you may want to keep your private key on a diskette, which you can insert like an old-fashioned key whenever you want to read or sign private information.

As another security precaution, consider assigning a different name to your private keyring file and then storing it somewhere other than in the default location. Use the Keys tab of the Options dialog box to specify a name and location for your private and public keyring files.

Your private and public keys are stored in separate keyring files. You can copy them to another location on your hard drive or to a diskette. By default, the private keyring (secring.skr) and the public keyring (pubring.pkr) are stored along with the other program files in your “PGP” folder; you can save your backups in any location you like.

Keys generated on a smart card cannot be backed up because the private portion of your keypair is non-exportable. (Keys can be generated on a smart card on Windows systems only.)

You can configure PGP Desktop to back up your keyrings automatically after you close PGP Desktop. Your keyring backup options can be set in the Keys tab of the Options dialog box (for Windows) and in the Keys section of the Preferences dialog box (for Mac OS X).

Backing up Your Private Key

 To back up your private key

1 In the Smart Keyrings item, click My Private Keys.

2 Select the icon representing your keypair.

3 From the File menu, select Export.

4 Type a name for the file in the Save As field and specify a location in the

Where field.

5 Select the Include Private Key(s) check box. This is important, because if

you do not do this, only your public key will be exported.

6 Click Save.

7 Copy the file to a secure location. This may be a CD which you carefully

archive, another personal computer, or a USB flash drive that you keep in a safe location. Please remember not to distribute this file to others, as it contains both your private key and your public key.

PGP® Desktop for Mac OS X Working with PGP Keys

Note: If you are in a PGP Universal Server-managed environment and your

key mode is SKM, you cannot export your key using this method. To export your keypair, ask your PGP Universal Server administrator to export it from the management console. To determine what your key mode is, see Key Modes (on page 115).

What if You Lose Your Key?

If you lose your key and do not have a backup copy from which to restore your key, you will never again be able to decrypt any information encrypted to your key. You can, however, reconstruct your key if your PGP administrator has implemented a key restoration policy for your company. For more information, see PGP Key Reconstruction (see " Server" on page contact your PGP administrator.

80, "If You Lost Your Key or Passphrase" on page 80) and

Reconstructing Keys with PGP Universal

Distributing Your Public Key

After you create your PGP Desktop keypair, you need to get your public key to those with whom you intend to exchange encrypted messages.

You make your public key available to others so they can send you encrypted information and verify your digital signature; and you need their public key to send encrypted messages to them.

You can distribute your public key in various ways:

 Publish your key on the PGP Global Directory (see "Placing Your Public Key

on a Keyserver" on page

Generally none of the other methods are necessary once your key is published to this directory.

 Include your public key in an email message (see "Including Your Public Key

in an Email Message" on page

 Export your public key or copy it to a text file (see "Exporting Your Public

Key to a File" on page

On Windows systems, you can also:

 Copy from a Smart Card directly to someone's keyring.

52).

53).

PGP® Desktop for Mac OS X Working with PGP Keys

Placing Your Public Key on a Keyserver

The best method for making your public key available is to place it on a public keyserver, which is a large database of keys, where anyone can access it. That way, people can send you encrypted email without having to explicitly request a copy of your key. It also relieves you and others from having to maintain a large number of public keys that you rarely use.

There are a number of keyservers worldwide, including the PGP Global Directory, where you can make your key available for anyone to access. If you are using PGP Desktop in a domain protected by a PGP Universal Server, your PGP administrator will have preconfigured PGP Desktop with appropriate settings.

When you’re working with a public keyserver, keep these things in mind before you send your key:

 Is this the key you intend to use? Others attempting to communicate with

you might encrypt important information to that key. For this reason, we strongly recommend you only put keys on a keyserver that you intend for others to use.

 Will you remember your passphrase for this key so you can retrieve data

encrypted to it or, if you don’t want to use the key, so you can revoke it?

 Other than the PGP Global Directory, once a key is up there, it’s up there.

Some public keyservers have a policy against deleting keys. Others have replication features that replicate keys between keyservers, so even if you are able to delete your key on one server, it could reappear later.

Most people post their public key to the PGP Global Directory right after they create their keypair. If you have already posted your key to the PGP Global Directory, you do not need to do it again. Under most circumstances, there is no need to publish your key to any other keyserver. Note also that other keyservers may not verify keys, and thus keys found on other keyservers may require significantly more work on your part to contact the key owner for fingerprint verification.

 To manually send your public key to a keyserver

1 Open PGP Desktop.

2 Ctrl+click the keypair whose public key you want to send to the keyserver.

3 Select Send Key To Server, then select the keyserver you want to send

the public key to from the list. If the keyserver you want to send your public key to is not on the list, see Working with Keyservers (on page 56).

Once you place a copy of your public key on a keyserver, it’s available to people who want to send you encrypted data or to verify your digital signature. Even if you don’t explicitly point people to your public key, they can get a copy by searching the keyserver for your name or email address.

PGP® Desktop for Mac OS X Working with PGP Keys

Many people include the Web address for their public key at the end of their email messages. In most cases, the recipient can just double-click the address to access a copy of your key on the server. Some people even put their PGP fingerprint on their business cards for easier verification.

Including Your Public Key in an Email Message

Another convenient method of delivering your public key to someone is to include it with an email message.

When you send someone your public key, be sure to sign the email. That way, the recipient can verify your signature and be sure no one has tampered with the information along the way. Of course, if your key has not yet been signed by any trusted introducers, recipients of your signature can only truly be sure the signature is from you by verifying the fingerprint on your key.

 To include your public key in an email message

1 Open PGP Desktop.

2 Open your email client, create a new message, and address it to the

person to whom you are sending your public key.

3 From PGP Desktop, drag and drop your keypair onto the body of the email

message.

4 Send the message.

If this method does not work for you, you can open PGP Desktop, select your

keypair, then select Edit > Copy. Open an email message, then paste the public

key into the body of the message. With some email applications you can simply drag your key from PGP Desktop into the text of your email message to transfer the public key information.

Exporting Your Public Key to a File

Another method of distributing your public key is to export it to a file and then make this file available to the person with whom you want to communicate securely.

There are three ways to export or save your public key to a file:

 Select your keypair, then select File > Export. Enter a name and a location

for the file, then click Save. Be sure not to include your private key along with your public key if you plan on giving this file to others.

 Ctrl+click the key you want to save to a file, select Export from the list,

enter a name and a location for the file, then click Save. Be sure not to include your private key along with your public key if you plan on giving this file to others.

PGP® Desktop for Mac OS X Working with PGP Keys

 Select your keypair, then select Edit > Copy. Open a text editor and select

Paste to insert the key information into the text file, and save the file. You

can then email or give the file to anyone you like. The recipient needs to use PGP Desktop on his or her system to retrieve the public key portion.

Getting the Public Keys of Others

Just as you need to distribute your public key to those who want to send you encrypted mail or verify your digital signature, you need to obtain the public keys of others to send them encrypted mail or verify their digital signatures.

There are multiple ways to obtain someone’s public key:

 Automatically retrieve the verified key from the PGP Global Directory

 Find the key manually on a public keyserver

 Automatically add the public key to your keyring directly from an email

message

 Import the public key from an exported file

 Get the key from your organization’s PGP Universal Server

Public keys are just blocks of text, so they are easy to add to your keyring by importing them from a file or by copying them from an email message and then pasting them into your public keyring in PGP Desktop.

Getting Public Keys from a Keyserver

If the person to whom you want to send encrypted mail is an experienced PGP Desktop user, it is likely that a copy of his or her public key is on the PGP Global Directory or another public keyserver. This makes it very convenient for you to get a copy of the most up-to-date key whenever you want to send him or her mail and also relieves you from having to store a lot of keys on your public keyring.

There are a number of public keyservers, such as the PGP Global Directory maintained by PGP Corporation, where you can locate the keys of most PGP users. If the recipient has not pointed you to the Web address where his or her public key is stored, you can access any keyserver and do a search for the user’s name or email address. This may or may not work, as not all public keyservers are regularly updated to include the keys stored on all the other servers.

If you are in a domain protected by a PGP Universal Server, then your PGP administrator may direct you to use the keyserver built into the PGP Universal Server. In this case, your PGP Desktop software is probably already configured to access the appropriate PGP Universal Server.

PGP® Desktop for Mac OS X Working with PGP Keys

Similarly, the PGP Universal Server is configured by default to communicate with the PGP Global Directory. Thus, the PGP ecosystem distributes the load of key lookup and verification.

 To get someone’s public key from a keyserver

1 Open PGP Desktop.

2 Click the PGP Global Directory item or the item of another keyserver you

want to search. The Search for Keys screen is displayed in the Work area.

3 Specify your search criteria, then click Search.

 If the keyserver you want to search is not shown, from the Keys

menu, select Add Keyserver, and configure it.

 You can search for keys on a keyserver by specifying values for

multiple key characteristics. You can also search for exclusions, such a using “User ID is not Charles” as your criteria.

The results of the search appear.

4 If the search found a public key you want to add to your keyring, Ctrl+click

it and select Add To Default Keying. The selected key is added to your keyring.

Tip: If you set the search criteria to look for a very common name (for

example, 'Name', 'contains', "John"), only the first match found is returned. This is by design, to prevent phishing (or harvesting keys from a keyserver). For common names or domains, you may have to enter the entire name or email address in order to find the correct key.

Getting Public Keys from Email Messages

A convenient way to get a copy of someone’s public key is to have that person attach it to an email message.

 To add a public key attached to an email message

1 Open the email message.

2 Double-click the .asc file that includes the public key. PGP Desktop

recognizes the file format and opens the Select key(s) dialog box.

3 If asked, specify to open the file.

4 Select the public key(s) you want to add to your keyring and click Import.

PGP® Desktop for Mac OS X Working with PGP Keys

Working with Keyservers

PGP Desktop understands the following kinds of keyservers:

 PGP Universal keyservers. If you are using PGP Desktop in a domain

protected by a PGP Universal Server, PGP Desktop is pre-configured to only communicate with the keyserver built into the PGP Universal Server with which it has a relationship. To PGP Desktop, this is a trusted keyserver, and PGP Desktop will automatically trust any key it finds on this keyserver unless the PGP Universal Server tells PGP Desktop that the key is not trusted—this can happen, for instance, when verifying signatures from remote keys.

 The PGP Global Directory. If you are using PGP Desktop outside of a

domain protected by a PGP Universal Server, PGP Desktop is pre-configured to communicate with the PGP Global Directory.

The PGP Global Directory is a free, public keyserver hosted by PGP Corporation. It provides quick and easy access to the universe of PGP keys. It uses next-generation keyserver technology that verifies the key associated with each email address (so that the keyserver doesn’t get clogged with unused keys, multiple keys per email address, forged keys, and other problems that plagued older keyservers) and it lets you manage your own keys, including replacing your key, deleting your key, and adding email addresses to your key. Using the PGP Global Directory significantly enhances your chances of finding the public key of someone with whom you want to send secured messages.

To PGP Desktop, the PGP Global Directory is a trusted keyserver, and PGP Desktop will automatically trust any key it finds there. During the initial connection to the PGP Global Directory, the PGP Global Directory Verification Key is downloaded, signed, and trusted by the key you publish to the directory. All of the keys verified by the PGP Global Directory are thus considered valid by your PGP Desktop.

 PGP Universal Services Protocol. The PGP Universal Services Protocol

(USP) is a SOAP protocol operating over standard HTTP/HTTPS ports. This is the default key lookup mechanism. If you are in a PGP Universal Server-managed environment, all key search requests as well as all other communications between the the PGP Universal Server and PGP Desktop use PGP USP.

 Other keyservers. In most cases, other keyservers are other public

keyservers. However, you may have access, through your company or some other means, to a private keyserver.

For more information about working with keyservers, see Keys Preferences (on

189).

page

PGP® Desktop for Mac OS X Working with PGP Keys

Using Master Keys

The Master Key List is a set of keys that you want added by default any time you are selecting keys for messaging, disk encryption, and PGP Zip. This saves you the step of dragging the keys that you regularly use into the Recipients field.

To use the Master Key List, select the Use Master Key List checkbox. You cannot add or remove keys from the Master Key List unless this box is selected.

Note: If you generated your key using the Setup Assistant, your key is

automatically added to the Master Key list. If you skipped key generation and imported your key into PGP Desktop, your key is not automatically added to the list.

Adding Keys to the Master Key List

 To add keys to the Master Key List

1 Open PGP Desktop.

2 Select PGP > Preferences.

3 Select the Master Keys icon.

4 Click the plus sign icon beneath the key list. The Select Master Keys dialog

box is displayed.

5 From the Name list on the left, select the key(s) that you want to use. Use

Shift+click or Cmd+click to select multiple keys.

PGP® Desktop for Mac OS X Working with PGP Keys

6 After selecting the keys you want, click OK. The keys you have selected

appear in the Master Key List.

Deleting Keys from the Master Key List

 To remove keys from the Master Key List

1 Open PGP Desktop.

2 Select PGP > Preferences.

3 Select the Master Keys icon.

4 Select the key(s) that you want to remove. You can Shift+click or

Cmd+click to select multiple keys.

5 Click the minus sign icon beneath the key list. The key(s) are removed.

Managing PGP Keys

This section describes how to manage keys with the PGP Desktop application.

Note: If you are using PGP Desktop in a PGP Universal Server-managed

In This Chapter

Examining and Setting Key Properties .................................................... 59

Adding and Removing Photographs ........................................................ 60

Managing User Names and Email Addresses on a Key .......................... 61

Importing Keys and X.509 Certificates .................................................... 62

Changing Your Passphrase...................................................................... 63

Deleting Keys, User IDs, and Signatures ................................................ 64

Disabling and Enabling Public Keys ......................................................... 65

Verifying a Public Key .............................................................................. 65

Signing a Public Key ................................................................................ 66

Granting Trust for Key Validations ........................................................... 68

Working with Subkeys............................................................................. 69

Working with ADKs ................................................................................. 74

Working with Revokers ........................................................................... 75

Splitting and Rejoining Keys .................................................................... 77

If You Lost Your Key or Passphrase ........................................................ 80

Protecting Your Keys ............................................................................... 83

Examining and Setting Key Properties

The Key Info dialog box displays everything there is to know about a key. The PGP Keys Work Area can display these important details about your keys:

 Name

PGP® Desktop for Mac OS X Managing PGP Keys

 Email address

 Validity

 Size

 KeyID

 Trust

 Creation date

 Expiration date

 ADK

 Status

 Key description

 Key usage

Note: If you are in a PGP Universal Server-managed environment and your

key mode is SKM, you cannot make changes to your key. In addition, SKM keys are set to never expire. To determine what your key mode is, see Key Modes (on page 115).

 To view a key’s properties

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Double-click the key with the properties you want to view. The Key

Properties dialog box for the key you selected is displayed.

Adding and Removing Photographs

You can include a photograph to your Diffie-Hellman/DSS and RSA keys.

Note: When you add or change key information, be sure to update it on the

keyserver so that your most current key is always available.

Caution: Although you can view for verification the photograph accompanied

with someone’s key, the digital fingerprint is the final word. Always check and compare it.

 To add your photograph to your key

1 Open PGP Desktop, then click My Private Keys.

2 Double-click the private key to which you are adding the photo. The Key

Info dialog box for the selected key is displayed.

PGP® Desktop for Mac OS X Managing PGP Keys

3 Click the plus sign icon under the current photo for the key. The Add Photo

dialog box is displayed.

4 Drag and drop, or paste, your photograph into the blank area of the Add

Photo dialog box.

Note: The photograph can be from the Clipboard, a JPG, or BMP file. For

maximum picture quality, crop the picture to 120 x 144 pixels before adding it. If you do not do this, PGP Desktop scales it for you.

5 Click OK. The Enter PGP Passphrase dialog box is displayed, unless the

passphrase for the key you are modifying is cached.

6 Enter your passphrase for the key you are modifying, then click OK. Your

photo ID is added to your private key.

 To view an enlargement of the photo

 Click the magnifying glass icon under the existing photo. A window

displaying an enlarged version of the photo ID appears. To remove the enlargement, click inside the window.

 To delete a photo ID

1 Click the minus sign icon under the existing photo. A confirmation dialog

box is displayed.

2 Confirm that this is your choice. The photo is removed from the key.

 To copy a photo ID

 Right-click the existing photo on the Key Properties dialog box and select

Copy Photo ID. You can then paste the photo into another key or into a

graphics program.

Managing User Names and Email Addresses on a Key

PGP Desktop supports multiple user names and email addresses on your keypair. These names and email addresses help others find your key so that they can send you encrypted messages.

 To add a new user name/address to your keypair

1 Open PGP Desktop, then double-click the appropriate key. The Key Info

dialog box for the key you double-clicked is displayed.

2 Click Add Email Address. The Add Name dialog box is displayed.

PGP® Desktop for Mac OS X Managing PGP Keys

3 Enter the new Full Name and Email Address in the appropriate fields,

then click OK. The Enter PGP Passphrase dialog box is displayed, unless the passphrase for the key you are modifying is cached.

4 Enter the private key passphrase of the key you are modifying, then click

OK. The new name is added to the end of the user name list associated

with the key.

Note: When you add or change information in your keypair, always

synchronize it with your keyserver so that your most current key is always available.

 To delete a name/email address from your keypair

1 From the list of keys, click the plus sign to the left of the key name to

expand the key.

2 Select the user ID you want to delete.

3 Press the Delete key on your keyboard. A confirmation dialog box is

displayed.

Tip: You can also select Edit > Delete (on Windows systems) or Edit >

Clear (on Mac OS X systems).

4 Click Delete. The user ID is deleted.

Importing Keys and X.509 Certificates

You can import PGP public keys and PKCS-12 X.509 certificates (a digital certificate format used by most Web browsers) to your PGP Desktop keyring, as well as PKCS-7 public X.509 certificates. You can also import Privacy Enhanced Mail (PEM) format X.509 certificates from your browser by copying and pasting into your public keyring.

There are many ways to import someone’s PGP public key and add it to your keyring. These methods include:

 Double-clicking the file on your system. If PGP Desktop recognizes the file

format, it will open and ask if you want to import the key(s) in the file.

 Choosing to import the key file in PGP Desktop.

 Dragging the file containing the public key onto the PGP Keys window.

PGP® Desktop for Mac OS X Managing PGP Keys

Importing X.509 Certificates Included in S/MIME Email Messages

If an X.509 certificate is included in an S/MIME email message sent to you, you can have PGP Desktop import the certificates to your key ring. The same settings you have specified when public keys are found apply to these certificates. If specified, PGP Desktop extracts and then imports the X.509 certificate to your keyring. If you want to encrypt email using imported certificates, be sure to manually sign the certificate.

To import X.509 certificates, choose PGP > Preferences. and select the Keys option. Then select Ask to save to my keyring or Save keys to my keyring.

Changing Your Passphrase

It’s a good practice to change your passphrase at regular intervals, perhaps every three months. More importantly, you should change your passphrase the moment you think it has been compromised, for example, by someone looking over your shoulder at the keyboard as you typed it in.

To change the passphrase for a split key, you must rejoin it first.

Tip: Changing your passphrase on your key does not change the passphrase

on any copies of the key (such as backups you may have made). If you think your key has been compromised, PGP Corporation recommends that you shred any previous backup copies and then make new backups of your key.

If you are in a PGP Universal Server-managed environment and your key mode is SKM, you cannot change the passphrase for your key. SKM keys are protected by a randomly generated passphrase (that is itself protected) and you are never prompted to enter a passphrase for an SKM key. To determine what your key mode is, see Key Modes (on page

 To change your private key passphrase

1 Open PGP Desktop, then double-click the appropriate key. The Key Info

dialog box for the key you double clicked is displayed.

2 Click Change Passphrase, then select Change Passphrase from the list of

commands displayed. The Enter PGP Passphrase dialog is displayed.

3 Enter the current passphrase for the private key, then click OK. The

Confirm PGP Passphrase dialog box is displayed.

4 Enter your new passphrase in the first text field.

5 Re-enter your passphrase in the Confirmation field.

115).

PGP® Desktop for Mac OS X Managing PGP Keys

6 Click OK. An information dialog box is displayed, informing you the

passphrase has been changed.

7 Click OK. The passphrase is changed.

Caution: If you are changing your passphrase because you feel that it has

been compromised, it is recommended that you shred all backup keyrings, then make a backup copy of the key with the new passphrase.

202).

Deleting Keys, User IDs, and Signatures

PGP Desktop gives you control over the keys on your keyrings, as well as the user IDs and signatures on those keys.

With public keys on your keyrings, you can delete entire keys, any user IDs on a key, and any or all signatures on a key.

With your keypairs, you can delete entire keypairs or any or all signatures, as well as delete user IDs from a keypair as long as that is not the only user ID on the keypair.

Note, however, that you cannot delete a user ID on a key if it is the only user ID, and you cannot delete self-signatures from keys.

 To delete a key from your PGP keyring

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Do one of the following:

 To delete a key, select the key, select Edit > Clear, then click OK on

the Confirmation dialog box. The key is deleted from your keyring.

 To delete a user ID (from a public key) or signature, click the triangle

to the left of the key with the User ID or Signature that you want to delete to display the user IDs and signatures. When you see the user ID or signature you want to delete, click the User ID, select Edit >

Clear, then click OK on the Confirmation dialog box. The user ID or

signature is deleted.

Remember that you cannot delete a user ID from a keypair.

PGP® Desktop for Mac OS X Managing PGP Keys

Disabling and Enabling Public Keys

Sometimes you may want to temporarily disable a public key on your keyring, which can be useful when you want to retain a public key for future use, but you don’t want it cluttering up your recipient list every time you send mail.

You cannot disable your keypairs.

 To disable a public key

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Double-click the public key you want to disable. The Key Info dialog box for

the key you selected is displayed.

3 Locate the Enabled field in the Key Properties.

 If the current Enabled setting is Yes, the key is enabled. To disable

the key, click Yes once. The Enabled field changes to No; the key is disabled.

 If the current Enabled setting is No, the key is disabled. To enable the

key, click No once. The Enabled field changes to Yes and the key is enabled.

A disabled key cannot be used to encrypt, sign, decrypt, or verify.

Tip: You can also synchronize keys on your keyring with the PGP Universal

Server. This option is used primarily to enable/disable public keys on your keyring. To do this, right-click (or Ctrl+click) a key and choose Synchronize.

Verifying a Public Key

It is difficult to know for certain whether a public key belongs to a particular individual unless that person physically hands the key to you on a removable media or you get the key from the PGP Global Directory. Exchanging keys on removable media is not usually practical, especially for users who are located many miles apart.

So the question remains: how can I make sure the public key I got from a public keyserver (not the PGP Global Directory) is really the public key of the person listed on the key? The answer is: you have to check the key’s fingerprint.

PGP® Desktop for Mac OS X Managing PGP Keys

There are several ways to check a key’s fingerprint, but the safest is to call the person and have them read the fingerprint to you over the phone. Unless the person is the target of an attack, it is highly unlikely that someone would be able to intercept this random call and imitate the person you expect to hear on the other end. You can also compare the fingerprint on your copy of someone’s public key to the fingerprint on their original key on a public server.

The fingerprint can be viewed in two ways: in a unique list of words or in its hexadecimal format.

 To check the digital fingerprint of a public key

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Double-click the public key with the fingerprint that you want to check. The

Key Info dialog box is displayed.

3 Locate the Digital Fingerprint in the second section of the Key Info dialog

box.

If necessary, click the triangle to face downward and display the fingerprint, which is shown either in hexadecimal format (10 sets of four characters per set) or word list format (four columns with five unique words per column).

4 Compare the fingerprint on the key with the original fingerprint. If the two

are the same, then you have the real key—otherwise, you likely do not.

The word list is made up of special authentication words that PGP Desktop uses and are carefully selected to be phonetically distinct and easy to understand without phonetic ambiguity. The word list serves a similar purpose as the military alphabet, which allows pilots to convey information distinctly over a noisy radio channel.

5 If you have a forged key, delete it.

6 Open your Web browser, navigate to the PGP Global Directory

(https://keyserver.pgp.com), and search for the real public key.

Signing a Public Key

When you create a keypair, the keys are automatically signed. Similarly, once you are sure a key belongs to the correct person, you can sign that person’s public key, indicating that you have verified the key. When you sign someone’s public key, a signature icon along with your user name is shown attached to that key.

If you import a keypair from a backup or from a different computer, that keypair needs to be signed.

PGP® Desktop for Mac OS X Managing PGP Keys

Note: If you are using PGP Desktop in a PGP Universal Server-managed

environment, key signing may be disabled.

 To sign a key

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Select the key you want to sign, then from the Keys menu, select Sign.

The Sign Key dialog box is displayed with the user name/email address and hexadecimal fingerprint displayed in the text box.

Tip: You can also Ctrl+click the key (or right-click it if you have a

two-button mouse). When the shortcut menu is displayed, select Sign.

3 Under Sign With Key, click to display and select which of your keys you

want to sign with.

4 To allow your signature to be exported with this key, select Allow

signature to be exported.

An exportable signature is one that is allowed to be sent to servers and travels with the key whenever it is exported. The checkbox indicates your approval that your signature be exported.

5 In the Select Items to Sign box, verify that you are signing the right key.

6 If you want to configure additional options, such as such as signature type

and signature expiration, click Options.

7 Choose a Signature Type to sign the public key with. Your choices are:

 Non-exportable. Use this signature when you believe the key is valid,

but you don’t want others to rely on your certification. This signature type cannot be sent with the associated key to a keyserver or exported in any way.

 Exportable. Use exportable signatures in situations where your

signature is sent with the key to the keyserver, so that others can rely on your signature and trust your keys as a result. This is equivalent to checking the Allow signature to be exported checkbox on the Sign

Keys menu.

 Meta-Introducer Non-Exportable. Certifies that this key, and any

keys signed by this key with a Trusted Introducer Validity Assertion, are fully trusted introducers to you. This signature type is non-exportable.

 Trusted Introducer Exportable. Use this signature in situations

where you certify that this key is valid, and that the owner of the key should be completely trusted to vouch for other keys. This signature type is exportable. You can restrict the validation capabilities of the trusted introducer to a particular email domain.

8 In the Expires field, select Never if you do not want this signature to

expire. Otherwise, select a date for it to expire.

PGP® Desktop for Mac OS X Managing PGP Keys

9 In the Advanced field, specify a maximum depth for trust and a domain

restriction:

 The Maximum Depth option enables you to identify how many levels

deep you can nest trusted-introducers. For example, if you set this to 1, there can only be one layer of introducers below the meta-introducer key.

 If you want to limit the trusted introducer’s key validation capabilities

to a single domain, enter the domain name in the Domain Restriction text box.

10 Click Sign. The Enter PGP Passphrase dialog box is displayed (if your

passphrase was not saved in the Keychain).

11 Type the passphrase of the signing key, if required. PGP Desktop does not

ask you to type your passphrase if it is cached.

12 Click OK. The key is signed.

Revoking Your Signature from a Public Key

You may, on occasion, want or need to revoke your signature from a key on your keyring.

 To revoke your signature

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Click the triangle to the left of the key from which you want to revoke your

signature. The signatures appear.

3 Click your signing key.

4 Select Edit > Revoke. A confirmation dialog box is displayed.

5 Verify that the Key ID and Name are the correct key (from which you want

to revoke your signature) and click OK. The PGP Enter PGP Passphrase for Key dialog box is displayed.

6 Enter your passphrase and click OK. Your signature is revoked from the

key.

Granting Trust for Key Validations

Besides certifying that a key belongs to someone, you can assign a level of trust to the owner of the keys indicating how well you trust them to act as an introducer for others, whose keys you may get in the future.

PGP® Desktop for Mac OS X Managing PGP Keys

This means that if you ever get a key from someone that has been signed by an individual whom you have designated as trustworthy, the key is considered valid even though you have not done the check yourself.

You must sign a key before you can set a trust level for it.

Public keys can be None, Marginal, or Trusted. Your keypairs can be None or

Implicit (meaning it is your own key and thus you trust it completely). You

shouldn’t have anyone else’s keypairs.

For more information about trusting keys, see An Introduction to Cryptography.

Note: If you are using PGP Desktop in a PGP Universal Server-managed

environment, the ability to grant trust to keys may be disabled.

To grant trust to a key

 To grant trust to a key

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Double-click the key for which you are granting trust. The Key Info dialog

box is displayed.

3 In the General Information section, click the current Trust field setting. A

menu of trust settings is displayed.

4 Select the desired setting.

Note: Selecting a Trust setting of None or Marginal is not intended to

indicate that an owner of a key is untrustworthy or dishonest. It means that you do not have enough information to be sure that a key’s owner or source is genuine.

Working with Subkeys

A PGP Desktop keypair consists of these elements:

 the Master Key, for signing only;

 one mandatory Subkey for encryption;

 one or more optional Separate Subkey(s) for signing, encryption, or

signing/encryption.

The Master Key is used by default for signing, while a subkey is always used for encryption. This can improve the security of a PGP Desktop keypair, as a separate encryption subkey can be revoked, removed, or added to the PGP Desktop keypair without affecting the Master Key or the signatures on it.

PGP® Desktop for Mac OS X Managing PGP Keys

In addition to the Master Key and the mandatory encryption subkey, you have the option of creating one or more additional subkeys for your PGP Desktop keypair. You can create any combination of subkeys that can be used for encryption only, for signing only, or for both encryption and signing.

You can view the subkeys of a keypair from the Key Properties dialog box. The Usage column indicates the function that a subkey performs:

Key

Description

Encryption subkeys display a blue padlock symbol.

Signing subkeys display a blue pen symbol.

Subkeys used for both encryption and signing display both symbols.

The default encryption subkey displays a small green checkmark in the upper left corner.

The default signing subkey displays a small green

PGP® Desktop for Mac OS X Managing PGP Keys

Key Description

check mark in the upper left corner.

Using Separate Subkeys

Here are some examples of how additional separate subkeys can be useful:

 Multiple encryption subkeys that are valid during different portions of the

keypair’s lifetime can increase security. You can create encryption subkeys that have the Start and Expiration dates set so that only one encryption subkey at a time is valid. For example, you could create several encryption subkeys that are valid only during one future year (make sure you specify correct dates). The Encryption Subkey in use then changes with the new year. This can be a useful security measure, as it provides an automatic way to switch to a new encryption key periodically without having to recreate and distribute a new public key. Expired subkeys display a key icon with a red clock.

Viewing Subkeys

 Separate signing subkeys are needed in regions where separate subkeys

for signing are required for legally-binding digital signatures.

The separate subkeys that you can create depend on the type of keypair that you are working with:

 For RSA keypairs, you can create subkeys for encryption, signing, and

encryption/signing.

 For Diffie-Hellman/DSS keypairs, you can create subkeys for encryption or

signing, but you cannot create subkeys that both encrypt and sign.

 For older PGP Legacy keypairs, subkeys are not supported.

You can view and change the subkey information on your keypairs. However, you can only view subkey information on the public keys on your keyring.

 To see what subkeys are on a key

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Double-click the key with the properties you want to view. The Key

Properties dialog box for the key you selected is displayed.

3 Click the triangle to the left of Subkeys. The Subkeys information for this

key is displayed.

PGP® Desktop for Mac OS X Managing PGP Keys

Creating New Subkeys

Most likely you will create new subkeys in the manner described in this section. However, you can also create subkeys when you first install PGP Desktop and are using the New Key wizard. For more information, see Using PGP Desktop for the First Time (on page

 To create new subkeys for a keypair

1 In the Subkeys section of the Key Properties dialog box, click the plus sign

icon. The New Subkey dialog box is displayed.

2 In the Use this subkey for area, select Encryption, Signing, or

Encryption and Signing, depending on how you want to use the new

subkey.

3 In the Key Size field, type a key size from 1024 to 4096 bits.

4 In the Start Date field, enter a date on which the subkey you are creating

becomes effective.

13).

5 In the Expiration Date field, select Never, or specify a date. This

information controls when the subkey expires.

Note: To avoid confusion when maintaining more than one subkey on

your keypair, try not to overlap the start and expiration dates of your subkeys.

6 Click Create. The Passphrase dialog box is displayed.

7 Enter your passphrase and then click OK. The subkey is created.

Note: When you add or change information in your keypair, update it on the

keyserver so that your most current key is always available. With the key selected in the Keys list, from the Keys menu, select Update Selection.

Specifying Key Usage for Subkeys

Each subkey can have its own key usage properties. For example, one subkey could be used for PGP WDE only, and another could be used for all other PGP Desktop functions.

An example of why you would want to set the key usage of a key is when you want to use a key for disk encryption only but you do not want to receive encrypted email. If you distribute your public key that does not allow for PGP Messaging, then email sent by another user would not be encrypted to your public key.

PGP® Desktop for Mac OS X Managing PGP Keys

Note: If you are in a PGP Universal Server-managed environment and your

key mode is SKM, you cannot make changes to the key usage flags. To determine what your key mode is, see Key Modes (on page 115).

 To specify key usage

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

Double-click the key with the properties you want to view. The Key Properties dialog box for the key you selected is displayed.

2 Click the Subkeys heading in the Key Properties dialog box. The Subkeys

for this key are displayed.

3 Double-click the subkey you want to change.

4 Click the arrow next to Subkey Usage Edit. The usage properties for the

key are displayed.

5 In the list displayed, select the PGP Desktop functions for which this key

can be used. A check next to the item indicates the key can be used for that function.

6 Click Close to save the subkey properties.

7 Click Close again to save the key properties.

Revoking Subkeys

 To revoke a subkey

1 In the Subkeys section of the Key Properties dialog box, select the subkey

2 Click Revoke (backslash-circle icon above the subkey list). A confirmation

3 Click OK to revoke the subkey. The Passphrase dialog box is displayed.

4 Type your passphrase, then click OK. The subkey is revoked and the icon

Removing Subkeys

 To remove a subkey

you want to revoke.

dialog box is displayed.

changes to a key with a red circle/slash.

1 In the Subkeys section of the Key Properties dialog box, select the subkey

you want to remove.

PGP® Desktop for Mac OS X Managing PGP Keys

2 Click Remove (a minus sign icon above the subkey list). A confirmation

dialog box is displayed.

3 Click OK to remove the subkey. The subkey is removed.

Working with ADKs

An additional decryption key (ADK) is a key generally used by security officers of an organization to decrypt messages that have been sent to or from employees within the organization.

Messages encrypted by a key with an ADK are encrypted to the public key of the recipient and to the ADK, which means the holder of the ADK can also decrypt the message.

ADKs are rarely used or needed outside of a PGP Universal Server-managed environment. Although your PGP administrator should not ordinarily need to use the additional decryption keys, there may be circumstances when it is necessary to recover someone’s email. For example, if someone is injured and out of work for some time, or if email records are subpoenaed by a law enforcement agency and the corporation must decrypt mail as evidence for a court case.

You can only modify ADKs on your keypairs.

Adding an ADK to a Keypair

 To add an ADK to a keypair

1 Open PGP Desktop, then click the Keys item. All keys on your keyring

appear.

2 Double-click the keypair to which you are adding the ADK. The Key Info

dialog box for the key you double-clicked is displayed.

3 If necessary, click the triangle icon, on the left side of the Additional

Decryption Keys section, so that it is pointing downward. The ADK

information for this key is displayed, if it has been configured.

4 Click the plus sign icon on the right side of the Additional Decryption

Keys section.

5 From the list displayed, select the key you want to use as the ADK.

6 Click OK. The PGP Enter PGP Passphrase for Key dialog box is displayed.

7 Enter the passphrase for the key to which you are adding the ADK, then

click OK. The ADK is added.

PGP® Desktop for Mac OS X Managing PGP Keys

Updating an ADK

 To update an ADK

1 Select the ADK you want to update from the list of ADKs. The selected

ADK highlights.

2 Click the down arrow icon. The ADK is updated.

Removing an ADK

 To remove an ADK

1 Select the ADK you want to remove from the list of ADKs. The selected

ADK highlights.

2 Click the minus sign icon. A PGP Warning dialog box is displayed, asking if

you are sure you want to remove the ADK.

3 Click OK to remove the ADK. The ADK is removed.

Working with Revokers

It is possible that one day you might forget your passphrase or lose your keypair (your laptop is stolen or your hard drive crashes, for example).

Unless you are also using Key Reconstruction and can reconstruct your private key, you would be unable to use your key again, and you would have no way of revoking it to show others not to encrypt to it. To safeguard against this possibility, you can appoint a third-party key revoker. The third-party you designate is then able to revoke your key just as if you had revoked it yourself.

This feature is available for both Diffie-Hellman/DSS and RSA keys.

You can only change revoker information on your keypairs. If a public key on your keyring has a revoker, you can see that information but you cannot change it.

PGP® Desktop for Mac OS X Managing PGP Keys

Appointing a Designated Revoker

 To add a designated revoker to your key

1 Open PGP Desktop, then select My Private Keys, under the Keys item. All

of the keys on your keyring appear.

2 Double-click the key to which you are adding a revoker. The Key Info dialog

box for the key you selected is displayed.

3 Click the plus sign icon on the right side of the Revokers section. The

Select key(s) dialog box is displayed.

4 Select the key you want to use as the revoker key, then click OK. A PGP

Warning dialog box is displayed, asking if you are certain that you want to grant revoker privileges to the selected key(s).

5 Click Yes to continue or No to cancel. The Enter PGP Passphrase for Key

dialog box is displayed.

6 Enter the passphrase for the keypair to which you are adding the revoker,

then click OK. A PGP Information dialog box is displayed.

Revoking a Key

7 Click OK. The selected key(s) is now authorized to revoke your key. For

effective key management, distribute a current copy of your key to the revoker(s) or upload your key to the keyserver.

If the situation ever arises that you no longer trust your personal keypair, you can revoke your key, which tells everyone to stop using your public key.

The best way to circulate a revoked key is to place it on a public keyserver.

 To revoke a key

1 Open PGP Desktop, then select My Private Keys under the Keys item. All

of the keys on your keyring appear.

2 Ctrl+click the key you want to revoke (or right-click if you are using a

two-button mouse).

3 In the shortcut menu, select Revoke. A Confirm Revocation dialog box is

displayed, asking if you are sure you want to revoke this key.

4 Click OK to confirm your intent to revoke the selected key or Cancel to

cancel.

5 Enter the passphrase for the keypair you are revoking, then click OK. When

you revoke a key, it is marked out with a red X to indicate that it is no longer valid.

PGP® Desktop for Mac OS X Managing PGP Keys

6 Synchronize the revoked key so everyone will know not to use the now

revoked public key.

Splitting and Rejoining Keys

Any private key can be split into shares among multiple “shareholders” using a cryptographic process known as Blakely-Shamir key splitting. This technique is recommended for extremely high security keys.

For example, PGP Corporation keeps a corporate key split between multiple individuals. Whenever we need to sign with that key, the shares of the key are rejoined temporarily.

Creating a Split Key

When you split a key, the shares are saved as files either encrypted to the public key of a shareholder or encrypted conventionally if the shareholder has no public key. After the key has been split, any attempts to sign or decrypt with it will automatically attempt to rejoin the key.

 To create a split key

1 Open PGP Desktop, then click the PGP Keys item. All of the keys on your

keyring appear.

2 Select the keypair you want to split. The selected keypair highlights.

3 Select Keys > Share Key > Make Shared. The Split Key dialog box is

displayed.

4 Add shareholders for the split key by dragging and dropping their keys in

the Key/User Name list.

5 To add a shareholder who does not have a public key, that person must be

physically present to enter their own passphrase. Click Add.

 Allow the shareholder to type in their passphrase twice, then click OK.

Unnamed User is displayed in the list.

 Double-click Unnamed User and enter a descriptive name for the

person or organization holding the shares.

6 To specify a location for the split shares, click Browse in the Share File

Destination Folder, then select the desired location.

7 When all of the shareholders are listed, you can specify the number of key

shares that are necessary to decrypt or sign with this key.

By default, each shareholder is responsible for one share. To increase the number of shares a shareholder possesses, double-click the number in the Shares column and enter the number of shares they control.

PGP® Desktop for Mac OS X Managing PGP Keys

8 Click Split Key. The Confirm Key Split dialog box is displayed.

9 Click OK to continue splitting the key. The Passphrase screen is displayed.

10 Enter the passphrase for the key being split, then click OK. A minimum of

six characters is required for this passphrase. A confirmation dialog box opens.

The key is split and the shares are saved in the location you specified. Each key share is saved with the shareholder’s name as the file name and a .shf extension.

11 Distribute the key shares to the owners, then delete the local copies of the

shares.

Be sure you keep the original key that was split. You will need to have this key before you can rejoin the split key for any decryption functions.

Rejoining Split Keys

Once a key is split among multiple shareholders, attempting to sign or decrypt with it causes PGP Desktop to attempt to rejoin the key automatically. There are two ways to rejoin the key: locally and remotely.

Rejoining key shares locally requires the shareholder’s presence at the rejoining computer. Each shareholder is required to enter the passphrase for their key share.

Rejoining key shares remotely requires the remote shareholders to authenticate and decrypt their keys before sending them over the network. The PGP Desktop Transport Layer Security (TLS) feature provides a secure link to transmit key shares, allowing multiple individuals in distant locations to securely sign or decrypt with their key share.

Caution: Before receiving key shares over the network, you should verify

each shareholder’s fingerprint and sign their public key to ensure that their authenticating key is legitimate.

Before you begin, be sure you have the original key that was split on the rejoining computer.

 To rejoin a split key

1 Contact each shareholder of the split key. To rejoin key shares locally, the

shareholders of the key must be present.

To collect key shares over the network, make sure the remote shareholders have PGP Desktop installed and are prepared to send their key share file. Remote shareholders must have:

 Their key share files and passwords.

 A keypair (for authentication to the computer that is collecting the key

shares).

PGP® Desktop for Mac OS X Managing PGP Keys

 A network connection.

 The IP address or Fully Qualified Domain Name of the computer that

is collecting the key shares.

2 At the rejoining computer, use the Finder to select the file(s) that you want

to sign or decrypt with the split key.

3 Ctrl+click the file(s) and select Sign or Decrypt from the PGP shortcut

menu. The Enter PGP Passphrase for Selected Key screen is displayed with the split key selected.

4 Click OK to reconstitute the selected key. The Key Share Collection screen

is displayed.

5 Do one of the following:

 If you are collecting the key shares locally, click Select Share File and

then locate the share files associated with the split key. The share files can be collected from the hard drive, a removable drive, or a mounted drive. Continue with the next step.

 If you are collecting key shares over the network, click Start

Network.

The Passphrase dialog box opens. In the Signing Key field, select the keypair that you want to use for authentication to the remote system and enter the passphrase. Click OK to prepare the computer to receive the key shares.

The status of the transaction is displayed in the Network Shares box. When the status changes to Listening, the PGP application is ready to receive the key shares.

At this time, the shareholders must send their key shares.

When a share is received, the Remote Authentication screen is displayed. If you have not signed the key that is being used to authenticate the remote system, the key will be considered invalid. Although you can rejoin the split key with an invalid authenticating key, it is not recommended. You should verify each shareholder’s fingerprint and sign each shareholder’s public key to ensure that the authenticating key is legitimate.

6 Click Confirm to accept the share file.

7 Continue collecting key shares until the value for Total Shares Collected

matches the value for Total Shares Needed on the Key Shares Collection screen.

8 Click OK. The file is signed or decrypted with the split key.

PGP® Desktop for Mac OS X Managing PGP Keys

If You Lost Your Key or Passphrase

If you lost your key, you can reconstruct your key so you can continue to encrypt and decrypt data. How you do this depends on if you are using PGP Desktop in a standalone environment or in a PGP Universal Server-managed environment.

If you forgot your passphrase, you can reset your passphrase. To do this, you answer correctly three of the five security questions you answered when you set up your key or created your security questions.

Reconstructing Keys with PGP Universal Server

This section applies only to PGP Desktop users in a PGP Universal Server-managed environment whose PGP administrator has configured key reconstruction support for their copy of PGP Desktop.

If you lose your key or forget your passphrase and do not have a backed up copy from which to restore your key, you will never again be able to decrypt any information encrypted to your key. You can, however, reconstruct your key if your PGP administrator has implemented a PGP key reconstruction policy for you, in which your key is encrypted and stored on a PGP Universal Server in such a way that only you can retrieve it.

The PGP Universal Server holding the key reconstruction data stores your key in such a way that only you can access it. Not even the PGP administrator has the ability to decrypt your key.

If your PGP administrator has configured support for key reconstruction, you will be prompted to enter additional “secret” information when you install PGP Desktop or when you create your security questions.

Once your key is on the server, you can restore it at anytime by selecting Keys

> I Lost My Key or Keys > I Forgot My Passphrase in PGP Desktop for

Windows, or Keys > Reconstruct in PGP Desktop for Mac OS X.

Tip: If you were not prompted to create your PGP questions during

installation of PGP Desktop, and your PGP Universal Server administrator allows local key reconstruction, you can manually create your questions. For more information, see Creating Your Security Questions (on page 81).

Creating Key Reconstruction Data

When you answer the PGP security questions, you are creating the key reconstruction data. In a standalone environment, this information is stored on your local disk in a .krb file. In a managed environment, you send the key reconstruction data to your company's PGP Universal Server whenever you install PGP Desktop or when you reset your key.

PGP® Desktop for Mac OS X Managing PGP Keys

Choose obscure personal questions with answers that you are not likely to forget. Your questions can be up to 95 characters in length. An example of a good question might be, “Who took me to the beach?” or “Why did Fred leave?” An example of a bad question would be, “What is my mother’s maiden name?” or “Where did I go to high school?”

When you have created and answered all five PGP questions, your private key is split into five pieces, using Blakely-Shamir key splitting. Three of the five pieces are needed to reconstruct the key. Each piece is then encrypted with the hash, the uniquely identifying number, of one answer. If you know any three answers, you can successfully reconstruct the whole key.

Creating Your Security Questions

Before you can reconstruct your key or create a new passphrase when you've forgotten it, you must create your security questions. You can customize the five security questions so that the answers are something that only you would know.

 To create your security questions

1 In PGP Desktop, click the Keys item and then select your key.

2 Select Keys > Create My PGP Questions. The PGP Security Question

Assistant is displayed.

3 When the Key Reconstruction screen dialog box is displayed, type five

questions that only you can answer in the Question fields (the default questions are examples only).

4 In the first Create Security Question screen, click the arrow for the first

field to select the question you want to use. Note that you can customize parts of the question in the next step.

PGP® Desktop for Mac OS X Managing PGP Keys

If you want to completely customize the question to create your own question, select Enter my own question.

5 For Personalize Your Question, click the arrows next to any of the text

that you can customize. For example, if you selected the first question, you can customize that question by changing "friend" to "boy" and "had a crush on" to "held hands with."

If you chose to create your own question, enter the question in this field. Be sure to enter a question that only you can know the answer to.

6 For Answer Your Question, enter the answer to this security question.

You can enter the answer using mixed upper- and lowercase letters, or use all one case (when you answer the question, the case will not matter).

A hint is displayed in this field that disappears once you start entering the answer. For example, to answer the question "Who was the first boy that I ever held hands with?", the hint is "Enter first and last name".

7 When you have defined your question and entered the answer, click Next

to continue. The Create Security Question 2 of 5 dialog box is displayed.

8 You are prompted to create and answer a total of five security questions.

Continue to follow the steps above to select the question, customize the question, and answer the question.

9 When you have entered all five questions and answers, the Enter PGP

Passphrase dialog box is displayed.

10 Enter the passphrase for your key and click OK.

11 You are then prompted to save the key reconstruction file. Enter the name

and location where you want to save the file and click Save.

12 Click Finish to exit the assistant.

You have now defined the five security questions. If you lost your key or forget your passphrase, you can reconstruct your key or reset your passphrase by answering three of these five questions.

Reconstructing Your Key if You Lost Your Key or Passphrase

If you have lost your key or have forgotten your passphrase, you can recover by reconstructing your key. You must first have created a set of security questions that only you can answer. For more information, see Creating Your Security Questions (on page 81).

 To reconstruct your key

1 In PGP Desktop, click the Keys item and then select your key.

2 Select Keys > Reconstruct.

 If you are managed by a PGP Universal Server, the PGP Passphrase

Assistant: Answer Security Questions dialog box is displayed.

PGP® Desktop for Mac OS X Managing PGP Keys

 If you are in a standalone environment, the Select Key Reconstruction

File dialog box is displayed. Select the .krb file that you saved when you created your security questions and click Open.

The Key Reconstruction dialog box is displayed.

3 Answer three of the five security questions correctly and click Continue.

The Confirm PGP Passphrase dialog box is displayed.

4 Enter and re-enter your new passphrase.

Select Show Keystrokes if you want to see the characters you type for your passphrase. Be sure no one can see what you type.

5 Click OK. Your key has been reconstructed.

Protecting Your Keys

PGP® Desktop for Mac OS X Managing PGP Keys

To prevent anyone who might happen to intercept your passphrase from using your private key, store your private key only on your own computer. If your computer is attached to a network, make sure that your files are not automatically included in a system-wide backup where others might gain access to your private key. Given the ease with which computers are accessible over networks, if you are working with extremely sensitive information, you may want to keep your private key on a flash drive, which you can insert like an old-fashioned key whenever you want to read or sign private information.

As another security precaution, consider assigning a different name to your private keyring file and then storing it somewhere other than in the default location.

You can configure PGP Desktop to back up your keyrings automatically after you close PGP Desktop. Your keyring backup options can be set in the Keys tab of the Options dialog box (for Windows systems) or the Preferences dialog box (for Mac OS X systems).

Tip: If you have changed your passphrase on your key, remember that it does

not change the passphrase on any copies of the key (such as backups you may have made). If you think your key has been compromised, PGP Corporation recommends that you shred any previous backup copies and then make new backups of your key.

Securing Email Messages

This section describes how to use PGP Desktop Email to automatically and transparently secure your email messages.

Note: If you are using PGP Desktop in a PGP Universal Server-managed

In This Chapter

How PGP Desktop Secures Email Messages ......................................... 85

Using Offline Policy ................................................................................. 89

Services and Policies ............................................................................... 90

Creating a New Security Policy ............................................................... 98

Working with the Security Policy List.................................................... 108

PGP Desktop and SSL ........................................................................... 113

Key Modes............................................................................................. 115

Viewing the PGP Log............................................................................. 118

Using PGP Scripts with Entourage 2008 ............................................... 119

How PGP Desktop Secures Email Messages

When secure email messaging is enabled, PGP Desktop monitors the email traffic between your email client and your mail server. Depending on the circumstances, PGP Desktop will intercede on your behalf to encrypt, sign, decrypt, or verify messages.

Once configured correctly—and it’s very likely PGP Desktop can do that for you automatically—you don’t have to do anything to encrypt and/or sign outgoing messages or to decrypt and/or verify incoming messages; the PGP Desktop messaging proxy does it for you.

How this happens is different for incoming and outgoing messages.

PGP® Desktop for Mac OS X Securing Email Messages

For incoming messages, PGP Desktop automatically evaluates all incoming email messages and takes the appropriate actions (described in the following section).

For outgoing messages, there are a range of actions that PGP Desktop can take on your behalf based on configured policies. A policy is a set of instructions (such as "In this circumstance, do this") that tells PGP Desktop what to do in specific situations. By combining these instructions, policies can be tailored to meet all of your email security requirements. PGP Desktop comes pre-configured with a set of policies that suit the needs of the vast majority of users. However, you are also provided with fine-grained control over these policies if you want to change them.

By default, when you are using PGP Desktop standalone and are sending an outgoing message, PGP Desktop looks for a key it can trust to encrypt the message. It looks first on the default keyring (called "All Keys" on Windows systems) or the local keyring (called "Keys" on Mac OS X systems) for the public key of the recipient. If it does not find such a key, it will, again by default, check the PGP Global Directory for a trusted key for the recipient. If it does not find a trusted key there, the message is sent in the clear, which is unencrypted. This default behavior, called Opportunistic Encryption, strikes a balance between protecting outgoing messages and making sure they get sent.

Creating new policies is covered in detail in Creating a New Security Policy (on page

If you are in a PGP Universal-protected domain, your local PGP Desktop policies determine how your messages are encrypted and when. For more information, consult with your organization’s PGP Universal Server administrator.

Incoming Messages

PGP Desktop manages incoming mail messages based on the content of the message. These scenarios assume standalone PGP Desktop, not in a domain protected by a PGP Universal server (in which case mail action policies set by your PGP Universal Server administrator can apply):

 Message not encrypted nor signed. PGP Desktop does nothing to the

 Message encrypted, but not signed. When PGP Desktop sees a

98).

content of these messages; it simply passes the message along to your email client.

message coming to you that is encrypted, it will attempt to decrypt it for you. To do this, PGP Desktop will check the local keyring for the private key that can decrypt the message. If the private key is not on the local keyring, PGP Desktop will not be able to decrypt it; the message will be passed to your email client still encrypted. If the private key is on the local keyring, PGP Desktop will decrypt it immediately if the passphrase for the private key is in memory (cached). If the passphrase is not cached, PGP Desktop will prompt you for the passphrase and decrypt the message when you supply the correct passphrase. Once a message is decrypted, PGP Desktop passes it to your email client.

PGP® Desktop for Mac OS X Securing Email Messages

If the PGP Desktop messaging proxy is turned off, PGP Desktop will not be able to decrypt incoming encrypted messages; it will pass them along to your email client still encrypted. It is recommended that you leave your messaging proxy on all the time if you expect to be sending and receiving encrypted messages. On is the default setting.

 Message signed, but not encrypted. PGP Desktop will search the local

keyring for a public key that can be used to verify the signature. If PGP Desktop cannot find the appropriate public key on the local keyring, it will try to search for a keyserver at keys.domain (where domain is the domain of the sender of the message), then the PGP Global Directory

https://keyserver.pgp.com), and finally any other configured keyservers. If

( PGP Desktop finds the right public key at any of these locations, it verifies the signature (or not, if the signature is bad) and passes the message to your email client annotated with information about the signature—information is also put into the PGP Log. If PGP Desktop cannot find the appropriate public key, it passes the message to your email client unverified.

 Message encrypted and signed. PGP Desktop goes through both of the

processes described above: first finding the private key to decrypt the message and then finding the public key to verify the signature. However, if a message cannot be decrypted, then it cannot be verified.

If PGP Desktop is unable to either decrypt or verify a message, you might want to consider contacting the sender of the message. If the message could not be decrypted, make sure the sender was using your real public key. If the message could not be verified, ask the sender to publish their key on the PGP Global Directory — older PGP versions or other OpenPGP products can access the web version of this directory at PGP Global Directory

https://keyserver.pgp.com) , or ask them to send their public key to you directly

( by email.

Note: PGP Desktop only encrypts by default to keys that are known to be

valid. If you did not get a key from the PGP Global Directory, you may need to verify its fingerprint with the owner and sign it for it to be used.

Understanding Annotations on Incoming Messages

When incoming email messages are received, PGP Desktop decrypts any encrypted portions and verifies any signatures. Then a snippet of text, called an annotation, is inserted into the processed email message to indicate what encryption and signatures were present. Any email message with at least partial protection (encrypted, signed, or both) receives an annotation. If an email message is completely unprotected (for example, the email is not encrypted or signed by the sender) then the message is not annotated.

You can choose three annotation levels:

PGP® Desktop for Mac OS X Securing Email Messages

 Maximum: Verbose Annotation. Adds annotations to your incoming

email detailing every action that PGP Desktop has taken during message processing.

 Medium: Failures and Successes. This option is the default. Provides

annotations when there has been a processing failure, such as unknown key, or unknown signer. The Medium setting provides annotations for all decrypted and/or signed email, but does not list individual attached files.

 Minimum: Failures Only. Only provides annotations when there has been

a processing failure, such as detecting an unknown key or unknown signer.

To specify the level of annotation you want to use, see Messaging Options (see

Messaging Preferences" on page 192).

In a PGP Universal Server-managed environment, your administrator may have specified the location of the annotation. The annotation can be "wrapped around" the message text (the default setting), or placed below the message text.

For more information on annotations, see PGP KB article 2039 (http://support.pgp.com/?faq=2039).

Outgoing Messages

Email messages that you send can be encrypted, signed, both, or neither. Because you probably have different combinations for different recipients or email domains, you need to create policies for all of your outgoing email message possibilities. Once correct policies are in place, your email messages are protected automatically and transparently.

If you are in a PGP Universal Server-managed environment, your PGP Desktop policies are controlled by the policies specified by your PGP Universal Server administrator. Your administrator may also have specified how to handle outgoing email messages if the PGP Universal Server is not available. These policies are called offline (or local) policies.

Securing Sent Items on IMAP Email Servers

If you are using an IMAP email server, messages in your Sent Items folder are typically stored on the mail server. IMAP email clients send the sent message copy over the network to the folder using the IMAP protocol. If the sent message is not encrypted, the message could be intercepted. PGP Desktop provides the ability for sent messages to be encrypted and/or signed as they are sent to the IMAP server.

In a PGP Universal Server-managed environment, your administrator may have specified that all messages in the Sent Items folder be secured.

PGP® Desktop for Mac OS X Securing Email Messages

In a standalone environment, you can specify if you want to secure the sent messages. To do this, choose Tools > Options (in PGP Desktop for Windows) or PGP > Preferences (in PGP Desktop for Mac OS X) and click the Messaging tab or item. Then specify if you want to encrypt, encrypt and sign, or just sign the messages.

Email messages are encrypted using your public PGP key.

When you access your Sent Items folder, and your key's passphrase is not cached, you are prompted to enter the passphrase.

If the name of the folder is not a name that PGP Desktop recognizes (for example, instead of "Sent Items" the folder is named "Outgoing Messages"), a message is displayed asking you confirm if the name of the folder is where your sent messages are typically stored. Note that the first message copied to this folder is not encrypted and/or signed, but that subsequent messages copied to this folder are.

Using Offline Policy

If you are using PGP Desktop in a PGP Universal Server-managed environment, the offline mail policy is defined by your PGP Universal Server administrator. This policy defines what happens to email messages when the PGP Universal Server is offline or cannot be reached by PGP Desktop.

 Block outbound messages. Your outbound messages are not sent. If the

messages can be queued by your mail client, they stay in the queue until the PGP Universal Server is available. If the messages cannot be queued, the email messages are blocked.

 Send outbound messages in the clear. You are prompted to choose if

you want to allow the email message to be sent unsecured. If you choose to send, the message is sent in the clear. If you choose not to send, the message is blocked.

 Follow standalone policy. PGP Desktop follows the standalone policy to

process your outbound messages. For more information, see Viewing Services and Policies (on page

For information on the notifiers you receive when any of the above occurs, see Outgoing PGP Desktop Notifier Messages for Offline Policy (on page 32).

Your PGP Universal Server administrator can specify how often your mail policies get downloaded to PGP Desktop. When you are in offline mode, the last downloaded offline mail policy remains in effect for processing your outbound email messages. If you have been in offline mode for a period of time that is longer than the grace period allowed for the offline standalone mail policy to be in effect, your administrator could have also specified how outgoing email should be processed. In this case, PGP Desktop can start blocking your outbound messages or the same offline standalone mail policy can be used for processing your outbound messages, depending on how policy is defined by your administrator.

91).

PGP® Desktop for Mac OS X Securing Email Messages

When you have been offline for some time, you can manually request a download of policy from the PGP Universal Server once you are back online. To do this when you are back online, select the PGP Desktop icon in the tray and then select Update Policy. The latest policies are downloaded from the PGP Universal Server and any client logs are uploaded to the server. The option to manually update a policy is available for managed users only.

If your PGP Universal Server administrator allows you to use standalone policies, see Creating a New Security Policy (on page

98).

Services and Policies

To understand how to use PGP Desktop to automatically and transparently protect your outgoing messages, you need to understand two terms: service and policy.

 Service. Information about one email account on your system and the

policies that apply to that account. In most cases, PGP Desktop will automatically create and configure a service for each email account on your system. In some circumstances, you may want to create and configure a service manually.

 Policy. A set of one or more instructions that tell PGP Desktop what to do

in specific situations. Policies are associated with services—often more than one (a policy can be reused by different services). Conversely, a service can (and usually does) have more than one policy.

When deciding how to handle a specific outgoing email message, PGP Desktop checks the policies configured for the service one at a time (from the top of the list going down). When it finds a policy that applies, it stops checking policies and implements the one that applies.

All new services are created with the following default policies:

 Encrypt and Sign Buttons. Specifies that email is both signed and

encrypted when both the Encrypt and Sign buttons are enabled in Microsoft Outlook 2002, 2003, or 2007. This policy is available only on PGP Desktop for Windows.

 Sign Button. Specifies that email is signed when the Sign button is

enabled in Microsoft Outlook 2002, 2003, or 2007. This policy is available only on PGP Desktop for Windows.

 Encrypt Button. Specifies that email is encrypted when the Encrypt

button is enabled in Microsoft Outlook 2002, 2003, or 2007. This policy is available only on PGP Desktop for Windows.

 Mailing List Admin Requests. Specifies that administrative requests to

mailing lists are sent in the clear; that is, not encrypted or signed.

 Mail List Submissions. Specifies that submissions to mailing lists are sent

signed (so they can be authenticated) but not encrypted.

PGP Desktop Instruction Manual

Specifications and Main Features

Frequently Asked Questions

User Manual

What's New in PGP Desktop for Mac OS X Version 10.1

Using this Guide

“Managed” versus “Unmanaged” Users

Conventions Used in This Guide

Who Should Read This Document

About PGP Desktop Licensing

About PGP Desktop Licensing

Checking License Details

If Your License Has Expired

Getting Assistance

Getting product information

Contact Information

PGP Desktop Basics

PGP Desktop Terminology

PGP Product Components

Terms Used in PGP Desktop

Conventional and Public Key Cryptography

Using PGP Desktop for the First Time

Installing PGP Desktop

System Requirements

Installing and Configuring PGP Desktop

Installing the Software

Using PGP Desktop with Apple Boot Camp

Upgrading the Software

Licensing PGP Desktop

Running the Setup Assistant

Integrating with Entourage 2008

Uninstalling PGP Desktop

Moving Your PGP Desktop Installation from One Computer to Another

Accessing PGP Desktop Features

PGP Desktop Main Screen

Using the PGP Desktop Icon in the Menu Bar

Using the PGP Dock Icon

Using the Mac OS X Finder

PGP Desktop Notifier alerts

PGP Desktop Notifier for Messaging

PGP Desktop and the Finder

Overview

Encrypt, Sign, or Encrypt and Sign

Shred

Decrypt/Verify

Mount or Unmount a PGP Virtual Disk Volume

Import a PGP Key

Add PGP Public Keys to Your Keyring

Extract the Contents of a PGP Zip Archive

Viewing the PGP Log

Working with PGP Keys

Viewing Keys

Creating a Smart Keyring

Creating a Keypair

Expert Mode Key Settings

Protecting Your Private Key

Protecting Keys and Keyrings

Backing up Your Private Key

What if You Lose Your Key?

Distributing Your Public Key

Placing Your Public Key on a Keyserver

Including Your Public Key in an Email Message

Exporting Your Public Key to a File

Getting the Public Keys of Others

Getting Public Keys from a Keyserver

Getting Public Keys from Email Messages

Working with Keyservers

Using Master Keys

Adding Keys to the Master Key List

Deleting Keys from the Master Key List

Managing PGP Keys

Examining and Setting Key Properties

Adding and Removing Photographs

Managing User Names and Email Addresses on a Key

Importing Keys and X.509 Certificates

Importing X.509 Certificates Included in S/MIME Email Messages

Changing Your Passphrase

Deleting Keys, User IDs, and Signatures

Disabling and Enabling Public Keys

Verifying a Public Key