PGP Desktop User's Guide

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PGP® Desktop for Windows

User's Guide

Version Information

PGP Desktop for Windows User's Guide. PGP Desktop Version 10.0.3. Released October 2010.

Copyright © 1991-2010 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 version 4.5 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 version 4.2.1 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 GNU Public License, available at http://www.cs.fsu.edu/~engelen/soaplicense.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

-- 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.

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.

Contents

About PGP Desktop 10.0 for Windows

What's New in PGP Desktop for Windows Version 10.0 1

What's New in PGP Desktop 10.0 2

Using this Guide 4

“Managed” versus “Unmanaged” Users 5

Conventions Used in This Guide 6 Who Should Read This Document 6 About PGP Desktop Licensing 6

Licensing PGP Desktop for Windows 7

Checking License Details 7

If Your License has Expired 9 Getting Assistance 10

Getting product information 10

Contact Information 11

PGP Desktop Basics 13

PGP Desktop Terminology 13

PGP Product Components 13

Terms Used in PGP Desktop 14 Conventional and Public Key Cryptography 16

Learning More About Cryptography 17 Using PGP Desktop for the First Time 17

Installing PGP Desktop 21

Before You Install 21

System Requirements 21

Citrix and Terminal Services Compatibility 22 Installing and Configuring PGP Desktop 22

Installing the Software 23

Upgrading the Software 23

Licensing PGP Desktop 25

Running the Setup Assistant 25 Uninstalling PGP Desktop 26 Moving Your PGP Desktop Installation From One Computer to Another 26

The PGP Desktop User Interface 29

Accessing PGP Desktop Features 29

The PGP Desktop Main Screen 30

Using the PGP Tray Icon 31

Using Shortcut Menus in Windows Explorer 33

PGP® Desktop for Windows Contents

Using the Start Menu 34 PGP Desktop Notifier alerts 34

PGP Desktop Notifier for Messaging 34

PGP Desktop Notifier for Disk features 37

Enabling or Disabling Notifiers 38 Viewing the PGP Log 39

Working with PGP Keys 41

Viewing Keys 41 Creating a Keypair 42

Passwords and Passphrases 44 Protecting Your Private Key 45

Protecting Keys and Keyrings 46

Backing up Your Private Key 46

What if You Lose Your Key? 47 Distributing Your Public Key 47

Placing Your Public Key on a Keyserver 48

Including Your Public Key in an Email Message 49

Exporting Your Public Key to a File 49

Copying from a Smart Card Directly to Someone’s Keyring 50 Getting the Public Keys of Others 50

Getting Public Keys from a Keyserver 51

Getting Public Keys from Email Messages 52 Working with Keyservers 52 Using Master Keys 53

Adding Keys to the Master Key List 54

Deleting Keys from the Master Key List 54

Managing PGP Keys 55

Examining and Setting Key Properties 55 Working With Photographic IDs 57 Managing User Names and Email Addresses on a Key 57 Importing Keys and X.509 Certificates 59

Using the Import Certificate Assistant 59 Changing Your Passphrase 61 Deleting Keys, User IDs, and Signatures 62 Disabling and Enabling Public Keys 62 Verifying a Public Key 63 Signing a Public Key 64

Revoking Your Signature from a Public Key 65 Granting Trust for Key Validations 66 Working with Subkeys 67

Using Separate Subkeys 68

Viewing Subkeys 69

Creating New Subkeys 70

Specifying Key Usage for Subkeys 70

PGP® Desktop for Windows Contents

Revoking Subkeys 72

Removing Subkeys 72 Working with ADKs 72

Adding an ADK to a Keypair 73

Updating an ADK 73

Removing an ADK 73 Working with Revokers 74

Appointing a Designated Revoker 74

Revoking a Key 75 Splitting and Rejoining Keys 75

Creating a Split Key 75

Rejoining Split Keys 76 If You Lost Your Key or Passphrase 78

Reconstructing Keys with PGP Universal Server 79

Creating Key Reconstruction Data 79

Reconstructing Your Key if You Lost Your Key or Passphrase 81 Protecting Your Keys 83

Securing Email Messages 85

How PGP Desktop Secures Email Messages 85

Incoming Messages 86

Outgoing Messages 88

Sending MAPI Email with Microsoft Outlook 88

Using the Sign and Encrypt Buttons in Microsoft Outlook 89 Using Offline Policy 90 Services and Policies 91

Viewing Services and Policies 92

Creating a New Messaging Service 94

Editing Messaging Service Properties 97

Disabling or Enabling a Service 98

Deleting a Service 98

Multiple Services 99

Troubleshooting PGP Messaging Services 99 Creating a New Security Policy 101

Regular Expressions in Policies 106

Security Policy Information and Examples 108 Working with the Security Policy List 112

Editing a Security Policy 112

Editing a Mailing List Policy 113

Deleting a Security Policy 117

Changing the Order of Policies in the List 118 PGP Desktop and SSL 118 Key Modes 120

Determining Key Mode 121

Changing Key Mode 122 Viewing the PGP Log 123

iii

PGP® Desktop for Windows Contents

Securing Instant Messaging 125

About PGP Desktop’s Instant Messaging Compatibility 125

Instant Messaging Client Compatibility 126 About the Keys Used for Encryption 127 Encrypting your IM Sessions 127

Viewing Email with PGP Viewer 129

Overview of PGP Viewer 129

Compatible Email Clients 130 Opening an Encrypted Email Message or File 130 Copying Email Messages to Your Inbox 132 Exporting Email Messages 132 Specifying Additional Options 132 Specifying Options in PGP Viewer 133 Security Features in PGP Viewer 134

Protecting Disks with PGP Whole Disk Encryption 135

About PGP Whole Disk Encryption 136

How does PGP WDE Differ from PGP Virtual Disk? 137 Licensing PGP Whole Disk Encryption 137

License Expiration 138 Prepare Your Disk for Encryption 138

Supported Disk Types 139

Supported Keyboards 140

Ensure Disk Health Before Encryption 142

Calculate the Encryption Duration 143

Maintain Power Throughout Encryption 144

Run a Pilot Test to Ensure Software Compatibility 144 Determining the Authentication Method for the Disk 145

Passphrase and Single Sign-On Authentication 145

Public Key Authentication 146

Token-Based Authentication 146

Two-Factor Authentication Using a USB Flash Device 146

Trusted Platform Module (TPM) Authentication 147 Setting Encryption Options 148

Partition-Level Encryption 149

Preparing a Smart Card or Token to Use For Authentication 149

Using PGP Whole Disk Encryption Options 152 Encrypting a Disk or Partition 154

Supported Characters for PGP WDE Passphrases 155

Encrypting the Disk 156

Encountering Disk Errors During Encryption 159 Using a PGP WDE-Encrypted Disk 159

Authenticating at the PGP BootGuard Screen 160

PGP® Desktop for Windows Contents

Selecting Keyboard Layouts 163 Using PGP WDE Single Sign-On 165

Prerequisites for Using Single Sign-On 165

Encrypting the Disk to Use Single Sign-On 166

Multiple Users and Single Sign-On 166

Logging in with Single Sign-On 166

Changing Your Passphrase With Single Sign-On 167

Displaying the Windows Login dialog box 167 Maintaining the Security of Your Disk 168

Getting Disk or Partition Information 168

Using the Bypass Feature 169

Adding Other Users to an Encrypted Disk or Partition 169

Deleting Users From an Encrypted Disk or Partition 170

Changing User Passphrases 171

Re-Encrypting an Encrypted Disk or Partition 172

If you Forgot Your Passphrase 173

Backing Up and Restoring 175

Uninstalling PGP Desktop from Encrypted Disks or Partitions 175 Working with Removable Disks 175

Encrypting Removable Disks 176

Using Locked (Read-Only) Disks as Read-Only 177

Moving Removable Disks to Other Systems 177

Reformatting an Encrypted Removable Disk 178 Using PGP WDE in a PGP Universal Server-Managed Environment 178

PGP Whole Disk Encryption Administration 178

Creating a Recovery Token 180

Using a Recovery Token 180 Recovering Data From an Encrypted Drive 181

Creating and Using Recovery Disks 181 Decrypting a PGP WDE-Encrypted Disk 183 Special Security Precautions Taken by PGP Desktop 184

Passphrase Erasure 184

Virtual Memory Protection 185

Hibernation vs Standby 185

Memory Static Ion Migration Protection 185

Other Security Considerations 185 Using the Windows Preinstallation Environment 186

Using PGP Whole Disk Encryption with IBM Lenovo ThinkPad Systems 186

Using PGP Whole Disk Encryption with the Microsoft Windows XP Recovery Console187

Using PGP Virtual Disks 189

About PGP Virtual Disks 190 Creating a New PGP Virtual Disk 191 Viewing the Properties of a PGP Virtual Disk 194 Finding PGP Virtual Disks 194 Using a Mounted PGP Virtual Disk 194

Mounting a PGP Virtual Disk 195

Unmounting a PGP Virtual Disk 195

PGP® Desktop for Windows Contents

Compacting a PGP Virtual Disk 196

Re-Encrypting PGP Virtual Disks 197 Working with Alternate Users 198

Adding Alternate User Accounts to a PGP Virtual Disk 198

Deleting Alternate User Accounts from a PGP Virtual Disk 198

Disabling and Enabling Alternate User Accounts 199

Changing Read/Write and Read-Only Status 200

Granting Administrator Status to an Alternate User 200 Changing User Passphrases 201 Deleting PGP Virtual Disks 201 Maintaining PGP Virtual Disks 202

Mounting PGP Virtual Disk Volumes on a Remote Server 202

Backing up PGP Virtual Disk Volumes 202

Exchanging PGP Virtual Disks 203 The PGP Virtual Disk Encryption Algorithms 203 Special Security Precautions Taken by PGP Virtual Disk 204

Passphrase Erasure 204

Virtual Memory Protection 205

Hibernation 205

Memory Static Ion Migration Protection 205

Other Security Considerations 206

Creating and Accessing Mobile Data with PGP Portable 207

Creating PGP Portable Disks 207

Creating a PGP Portable Disk from a Folder 208

Creating a PGP Portable Disk from a Removable USB Device 209

Creating Read/Write or Read-Only PGP Portable Disks 210 Accessing Data on a PGP Portable Disk 210

Changing the Passphrase for a PGP Portable Disk 211

Unmounting a PGP Portable Disk 212

Using PGP NetShare 215

About PGP NetShare 216

PGP NetShare Roles 218 Licensing PGP NetShare 218 Authorized User Keys 219 Establishing a PGP NetShare Admin (Owner) 219 "Blacklisted" and "Whitelisted" Files, Folders, and Applications 220

“Blacklisted” and Other Files You Cannot Protect 220

"Blacklisted" and "Whitelisted" Folders Specified by PGP Universal Server 221

Application-based Encryption and Decryption Bypass Lists 221 Working with Protected Folders 222

Choosing the Location for a Protected Folder 223

Creating a New PGP NetShare Protected Folder 224

Using Files in a PGP NetShare Protected Folder 227

Unlocking a Protected Folder 227

PGP® Desktop for Windows Contents

Determining the Files in a Protected Folder 228

Adding Subfolders to a Protected Folder 229

Checking Folder Status 229

Copying Protected Folders to Other Locations 230 Working with PGP NetShare Users 231

Adding a PGP NetShare User 231

Changing a User's Role 232

Deleting a User from a Protected Folder 233 Importing PGP NetShare Access Lists 234 Working with Active Directory Groups 235

Setting up PGP NetShare to Work with Groups 235

Refreshing Groups 236 Decrypting PGP NetShare-Protected Folders 236 Re-Encrypting a Folder 237 Clearing a Passphrase 238 Protecting Files Outside of a Protected Folder 238 Backing Up PGP NetShare-Protected Files 240 Accessing PGP NetShare Features using the Shortcut Menu 241 PGP NetShare in a PGP Universal Server-managed Environment 241 Accessing the Properties of a Protected File or Folder 243 Using the PGP NetShare Menus in PGP Desktop 244

The File Menu 244

The Edit Menu 244

The NetShare Menu 244

Using PGP Zip 247

Overview 247 Creating PGP Zip Archives 248

Encrypting to Recipient Keys 250

Encrypting with a Passphrase 252

Creating a PGP Self-Decrypting Archive (SDA) 254

Creating a Sign Only Archive 255 Opening a PGP Zip Archive 257 Opening a PGP Zip SDA 258 Editing a PGP Zip Archive 258 Verifying Signed PGP Zip Archives 260

Shredding Files with PGP Shredder 263

Using PGP Shredder to Permanently Delete Files and Folders 263

Shredding Files using the PGP Shredder Icon on Your Desktop 265

Shredding Files From Within PGP Desktop 265

Shredding Files in Windows Explorer 265 Using the PGP Shred Free Space Assistant 266

Scheduling Free Space Shredding 267

vii

PGP® Desktop for Windows Contents

Storing Keys on Smart Cards and Tokens 269

About Smart Cards and Tokens 269

Compatible Smart Cards 271

Recognizing Smart Cards 272 Examining Smart Card Properties 273 Generating a PGP Keypair on a Smart Card 273 Copying your Public Key from a Smart Card to a Keyring 275 Copying a Keypair from Your Keyring to a Smart Card 275 Wiping Keys from Your Smart Card 277 Using Multiple Smart Cards 277 Special-Use Tokens 278

Configuring the Aladdin eToken 279

Setting PGP Desktop Options 281

Accessing the PGP Options dialog box 281 General Options 282 Keys Options 284 Master Keys Options 287 Messaging Options 287

Proxy Options 290 PGP NetShare Options 293 Disk Options 294 Notifier Options 297 Advanced Options 299

Working with Passwords and Passphrases 303

Choosing whether to use a password or passphrase 303 The Passphrase Quality Bar 304 Creating Strong Passphrases 305 What if You Forget Your Passphrase? 307

Using PGP Desktop with PGP Universal Server 309

Overview 309 For PGP Administrators 310 Manually binding to a PGP Universal Server 311

Using PGP Desktop with IBM Lotus Notes 313

About Lotus Notes and MAPI Compatibility 313 Using PGP Desktop with Lotus Notes 314

Sending email to recipients inside your Lotus Notes organization 314

Sending email to recipients outside your Lotus Notes organization 314

viii

PGP® Desktop for Windows Contents

Binding to a PGP Universal Server 315

Pre-Binding 315

Manual Binding 315 Notes Addresses 316 Notes Client Settings 316

The Notes.ini Configuration File 317 Using Lotus Notes Native Encryption 317

Index 319

About PGP Desktop 10.0

for Windows

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

13). You should also understand conventional and

16).

In This Chapter

What's New in PGP Desktop for Windows Version 10.0.......................... 1

Using this Guide......................................................................................... 4

Who Should Read This Document............................................................. 6

About PGP Desktop Licensing................................................................... 6

Getting Assistance................................................................................... 10

What's New in PGP Desktop for Windows Version 10.0

Building on PGP Corporation’s proven technology, PGP Desktop 10.0 for Windows includes numerous improvements and the following new and resolved features.

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

What's New in PGP Desktop 10.0

PGP Desktop Version 10.0.3

 This release of PGP Desktop includes resolution for minor issues. No new

features are included in this release.

PGP Desktop Version 10.0.0

General

 Additional supported operating systems. PGP Desktop for Windows can

now be installed on Windows 7.

 New localized versions. PGP Desktop has been localized and can now be

installed in French (France) and Spanish (Latin America).

 Support for new smart cards. For both pre- and post-boot in PGP Desktop

for Windows:

 Axalto Cyberflex Access 32K V2 smart card

PGP Keys

 Giesecke and Devrient Sm@rtCafe Expert 3.2 personal identity

verification cards

 Oberthur ID-One Cosmo V5.2D personal identity verification cards

 SafeNet iKey 2032 USB token

 T-Systems Telesec NetKey 3.0 and TCOS 3.0 IEI cards

 Redesigned interface. The main user application window in PGP Desktop

for Windows has been redesigned.

 PGP Universal Server connectivity. Increased resiliency of PGP Desktop

when connectivity to the PGP Universal Server is dependent on a VPN connection or is otherwise intermittent.

 Enhanced Server Key Mode (SKM) keys. SKM keys now include the

entire key on your keyring. In addition, SKM keys can now be used for encryption functions such as disk and file encryption and decryption, as well as decrypting MAPI email messages when you are offline.

 Keyring location. In PGP Desktop for Windows, you can use environment

variables to specify the location of your keyrings.

 Key usage flags. Each subkey can now have its own key usage properties,

so that one subkey could be used for PGP WDE only, and another could be used for all other PGP Desktop functions. Set the key usage of a key when you want to use a key for disk encryption only but you do not want to receive encrypted email using that key.

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

 Universal Server Protocol (USP) key searches. The PGP Universal

Services Protocol (USP) is a SOAP protocol operating over standard HTTP/HTTPS ports. This is now 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 PGP Universal Server and PGP Desktop use PGP USP.

PGP Messaging

 PGP Viewer. Use PGP Viewer to decrypt and view legacy

IMAP/POP/SMTP email messages.

 Lotus Notes. PGP Desktop now provides the ability to encrypt mail

messages using Lotus Notes native encryption if PGP Desktop is configured to do so and the recipient is an internal Notes user.

 Lotus Notes. PGP Desktop now provides the ability to encrypt Lotus Notes

RTF-formatted email messages using PGP/MIME, S/MIME, or PGP Partitioned formats.

 Lotus Notes. PGP annotations in messages now honor the regional

settings for date and time stamp.

 Microsoft Outlook buttons added. Buttons enable you to manually add

encryption and/or your digital signature to your Outlook emails. This new feature provides compliance with digital signature laws that require showing intent to sign.

 Offline policy enhancements. In a managed environment, mail policy is

PGP Portable

 Previously available as a standalone option, PGP Portable is now included in

PGP Whole Disk Encryption

 Additional smart card compatibility. New cards added for pre-boot

 Personal Identity Verification (PIV) card support. Support has been

 Additional Keyboard Compatibility (Windows). A total of 50 international

now enforced even if you are offline and not connected to the PGP Universal Server or if the server itself is offline.

PGP Desktop. PGP Portable Disks can be created on Windows systems. This functionality requires a separate license.

authentication in PGP Whole Disk Encryption for Windows include Axalto Cyberflex Access 32K V2, Marx CrypToken USB token, SafeNet iKey 2032 USB token, and T-Systems T-Telesec NetKey smart card.

added in PGP Whole Disk Encryption for Windows for users with Giesecke and Devrient Sm@rtCafe Expert 3.2 and Oberthur ID-One Cosmo V5.2D personal identity verification cards.

language keyboards can now be used to log in at PGP BootGuard. For a list of all compatible keyboards, see the PGP Desktop for Windows User's Guide or online help.

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

 Full disk encryption support on Linux. PGP WDE for Linux provides full

disk encryption with pre-boot authentication on Ubuntu and Red Hat. For more information, see the PGP Whole Disk Encryption for Linux Command Line Guide.

 Local self recovery. PGP Desktop for Windows now provides a way for

you to access your encrypted drive from the PGP BootGuard screen if you have forgotten your passphrase. When configured, you won't have to contact your administrator for assistance.

 Multi-user enhancements. In an environment where multiple users may

access a group of computers, the PGP Universal Server administrator can define a PGP WDE Admin password. When you enter this password at the PGP BootGuard screen on a PGP Desktop for Windows system, you are prompted to enter your Windows passphrase and the disk is decrypted.

 Force encryption enhancements. When your PGP Universal Server

administrator changes policy to require that all disks be encrypted, the next time policy is downloaded to your system, the PGP WDE assistant is displayed so you can begin to encrypt your disk.

 Additional token support for PGP BootGuard. The Marx CrypToken USB

token can now be used at the PGP BootGuard for PGP Desktop for Windows.

 Extended ASCII character support. Extended ASCII characters can now

 Kanji characters. Kanji characters are now displayed correctly in the PGP

 Windows Server operating systems. PGP WDE can now be installed on

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.

be used when creating PGP WDE users.

BootGuard screen.

Windows Server operating systems (Windows Server 2003 and Windows Server 2008). For additional system requirements and best practices information on using PGP WDE on Windows Server systems, see PGP KB article 1737 (

http://support.pgp.com/?faq=1737).

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

“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

309).

Note: References to PGP Universal Server-managed environments do not

apply to the PGP Virtual Disk or PGP Virtual Disk Professional products.

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.

 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.

 Customized BootGuard. If you are using PGP Desktop in a PGP Universal

Server-managed environment, your PGP administrator may have customized the PGP Whole Disk Encryption BootGuard screen to include additional text or a custom image such as your organization's logo. The graphics included in this guide depict the default installation. Your actual login screen may look different if your administrator has customized the screen.

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

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 Windows 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.

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.

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

 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.

Licensing PGP Desktop for Windows

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.

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

details as described in Checking License Details (on page 7). If you need to authorize your copy of PGP Desktop, do so as described in Authorizing PGP Desktop for Windows (on page

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

8).

Checking License Details

 To see the details of your PGP Desktop license

1 Double-click the PGP Desktop icon in the system tray.

2 Select Help > License. The PGP Desktop License dialog box is displayed.

This dialog box displays the following details:

Item Description

License Type The name of the licensed product.

License Seats The number of seats available for this license.

License Expiration The date when the license will expire.

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

Item Description

Product Information The components that are active in your

license. Move your cursor over the product name to see information about the product and to find out if you are currently licensed to use it.

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

will be available to you (PGP Zip and Keys).

Authorizing PGP Desktop for Windows

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.

Note: Make sure your Internet connection is active before proceeding. If you

have no Internet connection, you must submit a request for a manual authorization.

 Before you begin

If you purchased PGP Desktop, you received an email order confirmation with an attached .PDF file.

1 Make a note of the name, organization, and license number you received in

the email order confirmation. These are shown in the section titled

Important Note in the .PDF. You will need these details during the

licensing process.

During configuration of your PGP Desktop software, you must type the name, organization, email address, and license number to authorize your copy of PGP Desktop with PGP Corporation's authorization server.

Note: Your license number also appears on the download page of your

PGP product.

Double-click the PGP Desktop icon in the System Tray.

2 Select Help > License. The PGP Desktop License dialog box is displayed.

3 Click Change License. The PGP Licensing Assistant dialog box is displayed.

4 Type the Name and Organization exactly as specified in your PGP email

order confirmation .PDF. These will be shown in the section titled

Important Note in the .PDF. If the Important Note section does not exist

in your .PDF, your first authorization attempt will set the name and organization permanently.

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

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

6 Type the email address again to confirm it.

Note: If you have previously authorized the same license number, you

must enter the same Name, Organization, and Email Address as you did the previous time. If you enter different information, authorization will fail.

7 Click Next.

8 Do one of the following:

 Type your 28-character license number in the provided fields (for

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

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 request a one-time, 30-day evaluation of PGP Desktop, select

Request a one-time 30 day Evaluation of PGP Desktop. When you

purchase a license, you can enter it any time before the end of the 30-day evaluation period. If you don’t enter a valid license, PGP Desktop will revert to unlicensed functionality when the 30-day evaluation period is over.

 To purchase a PGP Desktop license, select Purchase a license

number now. A Web browser will open and take you to the online

PGP Store.

 To use PGP Desktop without a license, select Use without a license

and disable most functionality. The only feature of PGP Desktop

you can use without a license is PGP Zip and Keys.

9 Click Next to authorize.

10 When PGP is authorized, the features enabled by your license will be

displayed. Click Next, and then click Finish 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 9.x section in the PGP Support Portal ( suggestions.

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.

https://support.pgp.com) for

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

PGP Desktop Email

 Outgoing email messages are no longer sent encrypted.

PGP NetShare

 PGP NetShare protected folders can be accessed however the protected

files remain encrypted. (To view the encrypted files, manually decrypt the folders and files.)

 New PGP NetShare protected folders cannot be created.

 Files moved into a protected folder are not encrypted.

 Keys cannot be added or removed from PGP NetShare protected folders.

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.

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 PGP Corporation Support Portal (

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

https://support.pgp.com).

https://support.pgp.com/?faq=589).

PGP® Desktop for Windows About PGP Desktop 10.0 for Windows

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....................................................................... 13

Conventional and Public Key Cryptography ............................................. 16

Using PGP Desktop for the First Time..................................................... 17

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 (see " Windows" 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.

Licensing PGP Desktop for

7).

PGP® Desktop for Windows 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 Windows 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 Windows 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.

41)). This is important because to send an

PGP® Desktop for Windows PGP Desktop Basics

Learning More About Cryptography

For more information about cryptography, see An Introduction to Cryptography, which was installed on your system when PGP Desktop was installed. It is available through the Start menu.

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 Windows 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 Windows 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.

 Use PGP NetShare to share files and folders securely and easily

among any number of people—with maximum access control.

Installing PGP Desktop

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

In This Chapter

Before You Install..................................................................................... 21

Installing and Configuring PGP Desktop.................................................. 22

Uninstalling PGP Desktop ........................................................................26

Moving Your PGP Desktop Installation From One Computer to Another26

Before You Install

This section describes the minimum system requirements for installing PGP Desktop on your Windows computer.

System Requirements

Before you begin the installation, verify that your system meets these minimum requirements:

 Microsoft Windows 2000 (Service Pack 4),Windows Server 2003 (Service

Pack 1 and 2), Windows XP Professional 32-bit (Service Pack 2 or 3), Windows XP Professional 64-bit (Service Pack 2), Windows XP Home Edition (Service Pack 2 or 3), Microsoft Windows XP Tablet PC Edition 2005 (requires attached keyboard), Windows Vista (all 32- and 64-bit editions, including Service Pack 1 and 2), Windows 7 (all 32- and 64-bit editions).

Note: The above operating systems are supported only when all of the

latest hot fixes and security patches from Microsoft have been applied.

PGP Whole Disk Encryption (WDE) is supported on all client versions above as well as the following Windows Server versions:

 Windows Server 2003 SP 2 (32- and 64-bit editions)

 Windows Server 2008 SP 1 and 2 (32- and 64-bit editions)

 Windows Server 2008 R2 (32- and 64-bit editions)

PGP® Desktop for Windows Installing PGP Desktop

For additional system requirements and best practices information on using PGP WDE on Windows Server systems, see PGP KB article 1737

http://support.pgp.com/?faq=1737).

(

 512 MB of RAM

 64 MB hard disk space

For information on compatible email, instant messaging, and anti-virus software, see the PGP Desktop10.0 for Windows Release Notes.

Citrix and Terminal Services Compatibility

PGP Desktop for Windows has been tested with the following terminal services software:

 Citrix Presentation Server 4.0

 Citrix Metaframe XP

 Windows 2003 Terminal Services

The following features of PGP Desktop for Windows are available in these environments, as specified:

 Email encryption is fully supported.

 PGP Zip functionality is fully supported.

 PGP Shred functionality is fully supported.

 PGP NetShare is fully supported.

 PGP Virtual Disks cannot be mounted at a drive letter over Citrix/TS, but can

be mounted at directory mount points on NTFS volumes.

 PGP Whole Disk Encryption is not supported.

 Smart cards are not supported.

For information on how to install PGP Desktop on a Citrix server, see PGP Support KB Article 832 (

https://support.pgp.com/?faq=832).

Installing and Configuring PGP Desktop

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

PGP® Desktop for Windows Installing PGP Desktop

Installing the Software

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

PGP Desktop.

 To install PGP Desktop on your Windows system

1 Locate the PGP Desktop installation program. The installer program is an

.MSI file, which your PGP administrator may have distributed to you using the Microsoft SMS deployment tool.

2 Double-click the PGP Desktop installer.

3 Follow the on-screen instructions.

4 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.

Upgrading the Software

Note: PGP Desktop for Windows and PGP Universal Satellite for Windows

cannot both be installed on the same system. The installation programs for both products detect the presence of the other program and end the installation process if the other product is found.

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

 PGP Desktop for Windows

 PGP Universal Satellite for Windows

If you are using Microsoft Windows XP with your computer, you can upgrade only to PGP Desktop 9.6 or later from PGP Desktop 8.x. If you are using a Microsoft Windows 2000 system, you can upgrade from PGP Desktop Versions

6.x, 7.x, or 8.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.

PGP® Desktop for Windows Installing PGP Desktop

Upgrading PGP Desktop

Do one of the following:

 From PGP Desktop 8.x for Windows: Follow the standard installation

process for PGP Desktop 10.0 for Windows.

PGP Desktop for Windows 8.x is automatically uninstalled, and PGP Desktop 10.0 for Windows is installed. Existing keyrings and PGP Virtual Disk files are usable in the upgraded version.

 From a version of PGP Desktop for Windows prior to 8.0: Manually

uninstall versions of PGP Desktop prior to 8.0 before beginning the installation of PGP Desktop 10.0 for Windows. Existing keyrings and PGP Virtual Disk files will be usable in the upgraded version.

Upgrading from PGP Universal Satellite

Do one of the following:

 From PGP Universal Satellite 1.2 for Windows or previous: Follow the

installation process for PGP Desktop 10.0 for Windows.

Checking for Updates

Existing versions of PGP Universal Satellite for Windows are automatically uninstalled, and PGP Desktop 10.0 for Windows will be installed. Existing settings will be retained.

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

Desktop 10.0 for Windows is an unsupported configuration. Neither program will work correctly. Uninstall both programs and then install only PGP Desktop.

 From PGP Desktop for Windows (Version 8.x) and PGP Universal

Satellite: Follow the installation process for PGP Desktop 10.0 for

Windows.

PGP Desktop and PGP Universal Satellite for Windows are automatically uninstalled, and then PGP Desktop 10.0 for Windows is installed. Existing keyrings and PGP Virtual Disk files are usable in the upgraded version.

When enabled, PGP Desktop checks for software updates automatically at the specified interval. The default is one day. If a newer version of PGP Desktop is available for download, a notification screen is displayed that lets you download the new version. When disabled, PGP Desktop does not automatically check for software updates. For more information, see General Options (on page

282).

Once you have downloaded the update, install the update by following the prompts.

This option requires an active Internet connection.

PGP® Desktop for Windows Installing PGP Desktop

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

environment, this option may be required. PGP Desktop then searches for updates on its associated PGP Universal Server.

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

the update.

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, dencrypt 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

When the installation of PGP Desktop is complete, you are prompted to restart your computer. Once the computer restarts, as soon as you see the Windows Desktop, the PGP Desktop Setup Assistant starts automatically. The Setup Assistant displays a series of screens that ask you questions—then uses your answers to configure PGP Desktop for you.

Based on a number of factors, the Setup Assistant for your system contains only those screens that are appropriate for your installation.

PGP® Desktop for Windows Installing PGP Desktop

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.

Uninstalling PGP Desktop

You can uninstall PGP Desktop using the PGP Desktop uninstaller, or by using Windows' Add or Remove Programs feature. The following procedure describes using the PGP Desktop uninstaller directly.

If you are upgrading from PGP Desktop 8.x or later, you do not have to uninstall PGP Desktop first. For more information, see Upgrading the Software (on page

23).

 To uninstall PGP Desktop

1 Click the Start menu and select Programs > PGP > Uninstall PGP

Desktop. A confirmation dialog box is displayed.

2 Click Yes to continue with the uninstall process. The PGP Desktop software

is removed from your system.

Keyring, PGP Virtual Disk, and PGP Zip (.pgp) files are not removed from your system, in case you decide to reinstall PGP Desktop in the future.

3 If prompted, restart your computer to complete the uninstall process.

Note: An alternative to uninstalling PGP Desktop is stopping PGP Desktop

background services. Doing this prevents PGP Desktop from protecting your email and instant messages, but both PGP Virtual Disk volumes and disks or partitions protected by PGP Whole Disk Encryption are still accessible. If you just need to turn off the PGP Desktop email or IM proxies, you can do that in the PGP Options dialog box (select Tools > Options, click the Messaging tab, and deselect the options as needed).

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:

PGP® Desktop for Windows Installing PGP Desktop

 To transfer your PGP Desktop installation to another computer

1 Uninstall PGP Desktop. To do this, choose Start > Programs > PGP >

Uninstall PGP Desktop. You can also use the Add/Remove Programs

functionality in the Windows Control Panel, which is the only way to remove PGP Desktop if you are running an older version of the program.

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 diskette or other removable media, and then copy them to the new computer. The default location for the keyring files is C:\Documents and Settings\<user>\My Documents\PGP\.

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 Corporation 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

Interface

This section describes the PGP Desktop user interface.

In This Chapter

Accessing PGP Desktop Features ...........................................................29

PGP Desktop Notifier alerts ..................................................................... 34

Viewing the PGP Log ...............................................................................39

Accessing PGP Desktop Features

There are four main ways to access PGP Desktop:

 PGP Desktop Main Window (see "The PGP Desktop Main Screen" on page

30)

 PGP Tray Icon (see "Using the PGP Tray Icon" on page 31)

 Shortcut Menus in Windows Explorer (see "Using Shortcut Menus in

Windows Explorer" on page

 Start Menu (see "Using the Start Menu" on page 34)

33)

PGP® Desktop for Windows The PGP Desktop User Interface

The PGP Desktop Main Screen

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

The PGP Desktop main screen includes:

The Menu bar. Gives you access to PGP Desktop commands.

The menus on the Menu bar change depending on which Control box is selected.

The PGP Keys Control Box. Gives you control of PGP keys.

The PGP Messaging Control Box. Gives you control over PGP

Messaging.

The PGP Zip Control Box. Gives you control of PGP Zip, as well

as the PGP Zip Assistant, which helps you create new PGP Zip archives.

The PGP Disk Control Box. Gives you control of PGP Disk.

The PGP Viewer Control Box. Gives you the ability to decrypt,

verify, and display messages outside the mail stream.

The PGP NetShare Control Box. Gives you control of PGP

NetShare.

The PGP Desktop Work area. Displays information and actions

you can take for the selected Control box.

PGP® Desktop for Windows The PGP Desktop User Interface

PGP Keys Find box. Use to search for keys on your keyring. As

you type text in this box, PGP Desktop displays search results based on either name or email address.

Each Control box expands to show available options, and collapses to save space (only the Control Box’s banner displays). Expand a Control Box by clicking its banner.

When expanded, the contents of Control Boxes change depending on what is appropriate for what you are working on, or what is selected. For example, when the PGP Keys Control Box is selected, if a public key is selected, the options Email this Recipient and Email this Key appear at the bottom of the PGP Keys Control Box. If a private key is selected, only Email this Key is displayed. If no key is selected, neither option is displayed.

To navigate around the PGP Desktop main screen, use the Tab key. Then use the Space key or Enter to select an option.

Note: Click Email this Recipient to open your system’s default email client

and create a new email using the address of the selected key. This makes it easy to send a message to someone on your keyring. Click Email this Key to open your system’s default email client and create a new email with the selected public key attached (the message is not addressed). This is useful for sending your public key, or a public key on your keyring, to someone who does not already have it.

Using the PGP Tray Icon

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

Tip: You can open PGP Desktop by double-clicking the PGP Tray icon.

The PGP Tray displays one of four icons:

 Normal operation (

are cached, message proxying is enabled, no other PGP operations are in progress.

 Cached passphrase (

one or more private key passphrases has been cached. Caching passphrases is an optional time-saving feature, in that you don’t have to type your passphrase if it’s cached to sign a key, for example, but it’s also a security risk in that if you leave your system with the passphrase cached, whoever walks up to your system could use PGP Desktop without having to type the appropriate passphrase.

): PGP Desktop is operating normally; no passphrases

): PGP Desktop is operating normally; additionally,

PGP® Desktop for Windows The PGP Desktop User Interface

 Message proxying disabled ( ): Proxying of email messages has been

disabled; incoming encrypted messages will not be decrypted or verified and outgoing messages will not be encrypted or signed. You can turn message proxying back on using the PGP Tray menu or the PGP Options.

 Busy (

): PGP Desktop is in the middle of an operation, such as encrypting a disk. When the operation is complete, the PGP Tray icon changes back to the appropriate icon.

When you right- or left-click on the PGP Tray icon, a menu is displayed giving you access to various options. Note that not all options may be available, depending on if you are a standalone or managed installation.

 Exit PGP Services. Stops PGP Desktop services on this computer. Be very

careful with this command; it will stop automatic encryption and decryption of email and instant messaging sessions.

If you stop the PGP Services, you can start them again by restarting your computer or by selecting PGP Desktop from the Start menu (Start >

Programs > PGP > PGP Desktop).

 About PGP Desktop. Displays information about the version of PGP

Desktop you are using, including licensing information.

 Check for Updates. Contacts the PGP Corporation update server to see if a

newer version of PGP Desktop is available for download. This option is available only in standalone installations.

 Help. Opens PGP Desktop’s integrated online help.

 Options. Opens the PGP Desktop Options dialog.

 View Notifier. Displays the last incoming and outgoing message notifiers.

 View PGP Log. Displays the PGP Desktop Log. Use the PGP Desktop Log

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

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

mail stream.

 Open PGP Desktop. Opens the PGP Desktop main screen. You can also

open PGP Desktop by double-clicking the PGP Desktop Tray icon.

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

This option is available only for managed installations.

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

passphrases and cached public keys.

Note: A cached passphrase is not cleared if you used a smart card or

token to access a PGP NetShare protected folder, and removed the smart card or token. To clear a cached passphrase, create a hot key. For more information, see Advanced Options (on page 299).

 Unmount PGP Virtual Disks. Unmounts all mounted PGP Virtual Disk

volumes.

PGP® Desktop for Windows The PGP Desktop User Interface

 Current Window. Lets you use PGP Desktop functionality (Decrypt &

Verify, Encrypt & Sign, Sign, Encrypt) on the contents of the current window.

 Clipboard. Lets you use PGP Desktop functionality (Decrypt & Verify,

Encrypt & Sign, Sign, Encrypt) on the contents of the Clipboard. Also lets you clear or edit the contents of the Clipboard.

Using Shortcut Menus in Windows Explorer

You can also access PGP Desktop functions using shortcut menus in Windows Explorer. Open Windows Explorer, right-click the items you want to work on, and select PGP Desktop from the shortcut menu.

Windows Explorer gives you access to PGP Desktop functions depending on the item that you right-clicked:

 Drive. If you right-click a drive on your system in Windows Explorer and

select PGP Desktop from the menu displayed, you can do the following to the drive:

 PGP Shred Free Space on it

 PGP Virtual Disk. If you right-click a mounted PGP Virtual Disk drive on

your system in Windows Explorer and select PGP Desktop from the menu displayed, you can do the following to the drive:

 Unmount the PGP Virtual Disk

 Locate the PGP Virtual Disk file (.pgd) in Windows Explorer

 Edit the PGP Virtual Disk properties

If you right-click the PGP Virtual Disk file (.pgd) in Windows Explorer for an unmounted disk, and select PGP Desktop from the menu displayed, you can also do the following:

 Compact unused space

 Use PGP Shred to securely delete the PGP Virtual Disk (note that this

also deletes all data on the disk)

 Re-encrypt the PGP Virtual Disk

 Folder. If you right-click a folder in Windows Explorer and select PGP

Desktop from the menu displayed, you can do the following to the folder:

 Add to new PGP Zip

 Create Self-Decrypting Archive of the contents in the folder

 Secure with a key or passphrase

 Decrypt & Verify it

 Add it to PGP NetShare

 Shred it

PGP® Desktop for Windows The PGP Desktop User Interface

 File. If you right-click a file in Windows Explorer and select PGP Desktop

from the menu displayed, you can do the following to the file, depending on what kind of file it is:

 If you select an unencrypted file, you can Secure it with a key or

passphrase, Sign, Shred, or Create a Self-Decrypting Archive

 If you select an encrypted file, you can decrypt/verify or Shred it

 If you select an unmounted PGP Virtual Disk volume (.pgd), you can

mount or edit it; if you select a mounted volume, you can unmount it

 If you select a PGP Zip (.PGP) file, you can Decrypt & Verify it, View it,

or Shred it

 If you select a PGP key file (.asc), you can decrypt/verify or Shred it.

If you select decrypt/verify, you are given the option of importing the file

 If you select a PGP public or private keyring file (PKR or SKR files,

respectively), you can add the keys in it to your keyring or Shred it

Using the Start Menu

You can access PGP Desktop through the Windows Start menu. To do this, select Start > Programs > PGP.

The Start menu provides you with access to:

 PGP Desktop documentation in English and other supported languages

 The PGP Desktop application

 Uninstalling PGP Desktop

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.

Note: The PGP Desktop Notifier feature also displays the status of the PGP

Whole Disk Encryption and PGP NetShare features on your computer. For more information, see PGP Desktop Notifier for Disk features (on page 37).

PGP Desktop Notifier for Messaging

Use the PGP Desktop Notifier for Messaging feature to:

PGP® Desktop for Windows The PGP Desktop User Interface

 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.

 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 (on page

297).

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.

PGP® Desktop for Windows The PGP Desktop User Interface

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).

You can also set PGP Desktop to include Block and Send buttons in the Notifier box.

 To manage the outgoing email with this Notifier

1 In the PGP Outgoing Message Notifier box, do the following:

 To stop this email message from being sent, click Block. Note this

blocks only this outgoing email message; future email messages to this sender can be sent.

 To send this message, even though the recipient’s key cannot be

found, click Send.

 To continue to delay a message from being processed, hover your

cursor over the Notifier box. When you move your cursor away from the Notifier box, the message is then processed using the default rule.

 In Notifier options, the Delay outbound mail for setting specifies

how long (in seconds) the Notifier gives you before it sends the mail without your intervention. The Notifier displays a countdown before it sends your mail.

2 To view additional information, including the Action, Recipient, Policy, and

Signing Key, click More.

It is not necessary for you to view this additional information unless you want to see it. To hide it again, click Less.

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® Desktop for Windows The PGP Desktop User Interface

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.

PGP Desktop Notifier for Disk features

The PGP Desktop Notifier for Disk features keep you informed when you are working with the PGP NetShare and the PGP Whole Disk Encryption features.

Note: The PGP Desktop Notifier feature also displays the status of incoming

and outgoing email messages on your computer. For more information, see PGP Desktop Notifier for Messaging (on page 34).

PGP NetShare

When used with PGP NetShare, the PGP Desktop Notifier feature alerts you to these things:

 Actions taken to a shared folder.

 Location of the affected folder.

 Name of the affected folder.

 Who performed the action.

PGP Whole Disk Encryption

When used with the PGP Whole Disk Encryption feature, the PGP Desktop Notifier feature alerts you to these things:

 The disk being encrypted.

 The size and type of disk.

PGP® Desktop for Windows The PGP Desktop User Interface

 Status of the encryption process.

Enabling or Disabling Notifiers

 To enable or disable Notifiers

1 Open PGP Desktop and select Tools > PGP Options.

2 Click the Notifier tab.

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 Lower Right.

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

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.

91).)

 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.

PGP® Desktop for Windows The PGP Desktop User Interface

 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.

Viewing the PGP Log

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

 To view the PGP Log

1 To view logs, you must turn on logging. To do this, in PGP Desktop select

Tools > Enable Logging.

2 Do one of the following:

 Click the PGP Desktop system tray icon and select View PGP Log

from the shortcut menu. The PGP Log opens in a new window.

 In PGP Desktop, select Tools > View Log. The PGP Log opens in a

new window.

 In PGP Desktop, click the PGP Messaging control box and then click

PGP Log. The PGP Log is displayed in the application window.

3 To change the view options or filter on specific logging information, do the

following:

 Click the arrow for View log for to select the days of the logs you

want to view.

 Click the arrow for View topic to select the types of logs you want to

view. Choose from All, PGP, Email, IM, Whole Disk, NetShare,

Zip/SDA, or Virtual Disk.

 Click the arrow for View level to select the minimum severity of log

entries you want to view. Choose from Error, Warn, Info, or Verbose.

To view Verbose logs, the PGP Log view window must remain open. When you close the window, the level of logging reverts back to the default level, Info. Note that Verbose can result in some large log files.

4 When you are finished viewing the log:

 To save a copy of the PGP Log, click Save.

 To clear the entries in the PGP Log, click Shred.

 To exit the PGP Log window, click Close.

PGP® Desktop for Windows The PGP Desktop User Interface

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 ...........................................................................................41

Creating a Keypair ....................................................................................42

Protecting Your Private Key ..................................................................... 45

Distributing Your Public Key..................................................................... 47

Getting the Public Keys of Others ........................................................... 50

Working with Keyservers.........................................................................52

Using Master Keys................................................................................... 53

Viewing Keys

To view the keys on the local keyring, open PGP Desktop and click on the PGP Keys Control box. Then click:

 All Keys. Shows all PGP keys on your keyrings.

 My Private Keys. Shows only the private keys on your keyrings.

 Search for Keys. Lets you search for keys on your keyrings based on

criteria you specify.

 Smart Card Keys. If you have a smart card on your system, you also have

this option.

PGP® Desktop for Windows Working with PGP Keys

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

 If a public key is selected in any view of the PGP Keys on your keyrings, the

option to Email this Recipient is available in the PGP Keys Control box.

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

is not on your local keyrings, the option Add to my Keyring is available in the PGP Keys Control box.

 To see the properties of any key displayed in the work area, just

double-click any part of the key listing to display the Key Properties dialog box for that key.

When you perform a search, the option Save this Key Search is available in the PGP Keys Control box, so you can save the results for later access.

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 Make sure the PGP Keys Control box is selected.

2 Select File > New PGP Key or press Ctrl+N. The first screen of the PGP

Key Generation Assistant is displayed.

3 Read the information on this screen.

4 If you want to generate your new PGP keypair on a token or smart card,

make sure the token or smart card is connected to the system and then select the box labeled Generate Key on Token: [name of smart card or

token on system]. For more information about smart cards and tokens,

see Storing Keys on Smart Cards and Tokens (on page 269).

5 Click Next. The Name and Email Assignment screen is displayed.

PGP® Desktop for Windows Working with PGP Keys

6 Type your real name in the Full Name field and your correct email address

in the Primary Email field. It is not absolutely necessary to type 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.

7 If you would like to add more email addresses to the key you are creating,

click More and type them in the fields that appear.

8 To specify advanced settings for the key you are creating, click Advanced.

The Advanced Key Settings dialog box is displayed. Use this dialog box to specify the key type and size, expiration, and other settings.

9 Select settings for the following:

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

 Generate separate signing subkey. Select this box if you need a

separate subkey for signing. A separate Signing Subkey is created along with the new keypair. You can also create additional signing or encryption subkeys any time after the new key has been created. For more information about separate Signing and Encryption Subkeys, see Working with Subkeys (on page

67).

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

more secure it is, but the longer it will take to generate. Some smart cards and tokens limit key size to 1024 bits.

 Expiration. Select Never or specify a date on which the keypair you

are creating will expire.

 Allowed Ciphers. Deselect any cipher 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 algorithm is specified. Only a cipher that is allowed can be selected as preferred.

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

are creating to support.

 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.

10 Click OK to close the Advanced Key Settings dialog box.

11 Click Next.

12 If you are part of a PGP-Universal managed environment, you may see the

Organization Settings screen, which displays keys your PGP administrator has configured to add to your copy of PGP Desktop (such as your organization’s Additional Decryption Key (ADK) or Organization Key).

The Passphrase Assignment screen is displayed.

PGP® Desktop for Windows Working with PGP Keys

13 Type the passphrase you want to use to maintain exclusive access to the

private key of the keypair being created.

14 To confirm your entry, press Tab to advance to the Confirmation field, then

type the same passphrase again. For information on the Passphrase Quality Bar, see The Passphrase Quality Bar (on page

Note: Normally, as an added level of security, the characters you type for

the passphrase do not appear on the screen. However, if you are sure that no one is watching, and you want to see the characters of your passphrase as you type, select the Show Keystrokes checkbox.

Warning: 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.

15 Click Next to begin the key generation process. PGP Desktop generates

your new keypair.

This process can take several minutes.

16 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.

304).

17 Read the text on the screen and click Next to add your new key to the PGP

Global Directory (recommended). Click Skip if you want to prevent the public key from being posted to the PGP Global Directory.

18 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 Control box.

Caution: Consider backing up your private key to a safe location at this

point. Your private key is very important, and losing it could have catastrophic consequences once you have data that is encrypted to it. See Protecting Your Private Key (on page 45).

Passwords and Passphrases

Encrypting a file and then finding yourself unable to decrypt it is a painful lesson in learning how to choose a passphrase you will remember.

Most applications require a password between three and eight letters. Using a single-word passphrase is generally a bad practice, and is discouraged. A single word password is vulnerable to a dictionary attack, which consists of having a computer try all the words in the dictionary until it finds your password. You can imagine simple enhancements to dictionary attacks which manage to find broad arrays of passwords even when slightly modified from dictionary terms.

PGP® Desktop for Windows Working with PGP Keys

To protect against this manner of attack, it is widely recommended that you create a word that includes a combination of upper and lowercase alphabetic letters, numbers, punctuation marks, and spaces. This results in a stronger password, but an obscure one that you are unlikely to remember easily.

Trying to thwart a dictionary attack by arbitrarily inserting a lot of non-alphabetic characters into a passphrase makes your passphrase too easy to forget and could lead to a disastrous loss of information because you can’t decrypt your own files. A multiple word passphrase is less vulnerable to a dictionary attack. However, unless the passphrase you choose is something that is easily committed to long-term memory, you are unlikely to remember it verbatim.

Picking a phrase on the spur of the moment is likely to result in forgetting it entirely. Choose something that is already residing in your long-term memory. It should not be something that you have repeated to others recently, nor a famous quotation, because you want it to be hard for a sophisticated attacker to guess. If it’s already deeply embedded in your long-term memory, you probably won’t forget it. Of course, if you are reckless enough to write your passphrase down and tape it to your monitor or put it in your desk drawer, it won’t matter what you choose.

For more information, see Working with Passwords and Passphrases (on page

303).

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

46).

page

 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.

61).

PGP® Desktop for Windows Working with PGP Keys

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.

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 PGP Keys control box, click My Private Keys.

2 Select the icon representing your keypair.

PGP® Desktop for Windows Working with PGP Keys

3 Select File > Export.

4 Type a name for the file.

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 (which has an .asc extension) to a secure location. This may

be a compact disc 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.

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 120).

What if You Lose Your Key?

If you lose your key 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 key restoration policy for your company. For more information, see PGP Key Reconstruction (see " Server" on page contact your PGP administrator.

79, "If You Lost Your Key or Passphrase" on page 78) and

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.

Reconstructing Keys with PGP Universal

48).

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

in an Email Message" on page

49).

PGP® Desktop for Windows Working with PGP Keys

 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:

49).

 Copy from a Smart Card directly to someone's keyring (see "

Smart Card Directly to Someone’s Keyring" on page

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.

Copying from a

50).

 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 Make sure the PGP Keys Control box is selected.

3 Right-click the keypair whose public key you want to send to the keyserver.

PGP® Desktop for Windows Working with PGP Keys

4 Select Send To and 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 lets you know when the public key is successfully copied to the keyserver.

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.

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.

52). PGP Desktop

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 In PGP Desktop, make sure the PGP Keys Control box is selected.

2 Right-click the keypair whose public key you want to include in an email

message.

3 Select Send To and then select Mail Recipient. Your email application

opens with your key information already in place.

4 Address the message and send it.

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

PGP® Desktop for Windows Working with PGP Keys

 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.

 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.

Copying from a Smart Card Directly to Someone’s Keyring

Another method of distributing your public key—if you have it on a smart card—is to copy it from the smart card directly to someone’s keyring.

For more information about how to do this, see Copying your Public Key from a Smart Card to a Keyring (on page 275).

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.

PGP® Desktop for Windows Working with PGP Keys

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.

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 and highlight the PGP Keys Control box.

2 Choose Search for Keys from the PGP Keys Control box. The Search for

Keys screen is displayed in the Work area.

3 Specify your search criteria, then click Search. If you want to search only a

specific keyserver, click in the Search field and select the keyserver. If the keyserver you want to search is not currently on the list, select Edit

Keyserver List and add it.

You can search for keys on a keyserver by specifying values for multiple key characteristics. The inverse of most operations is also available. For example, you may search 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, click Add

to My Keying in the PGP Keys Control box. 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.

PGP® Desktop for Windows Working with PGP Keys

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.

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 preconfigured 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 address for your PGP Universal keyserver may look like

https://keyserver.example.com.

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

domain protected by a PGP Universal Server, PGP Desktop is preconfigured to communicate with the PGP Global Directory (https://keyserver.pgp.com).

The PGP Global Directory is a free, public keyserver hosted by PGP Corporation and 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 the keyserver does not fill up with unused keys, multiple keys per email address, forged keys, and other problems that plagued older keyservers) and 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.

PGP® Desktop for Windows Working with PGP Keys

To PGP Desktop, the PGP Global Directory is a trusted keyserver, and PGP Desktop automatically trusts 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. The PGP Global Directory key is also added to your keyring. All of the keys verified by the PGP Global Directory are thus considered valid by 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 Options (on

284).

page

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, PGP NetShare, and PGP Zip. This saves you the step of dragging the keys that you regularly use into the

Recipients field.

PGP® Desktop for Windows Working with PGP Keys

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 In PGP Desktop, select Tools > Options.

2 Select the Master Keys tab.

3 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.

4 Click Add. The Select Master Keys dialog box is displayed.

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

Use Shift+click or Ctrl+click to select multiple keys.

6 After selecting the keys you want, click Add.

Tip: If there are any keys in the Keys to Add list on the right that you do

not want to include, select them and click Remove.

7 When you have finished selecting keys, 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 In PGP Desktop, select Tools > Options.

2 Select the Master Keys tab.

3 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.

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

to select multiple keys.

5 Click Remove. 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.....................................................55

Working With Photographic IDs ..............................................................57

Managing User Names and Email Addresses on a Key ..........................57

Importing Keys and X.509 Certificates ....................................................59

Changing Your Passphrase ...................................................................... 61

Deleting Keys, User IDs, and Signatures................................................. 62

Disabling and Enabling Public Keys .........................................................62

Verifying a Public Key............................................................................... 63

Signing a Public Key.................................................................................64

Granting Trust for Key Validations ...........................................................66

Working with Subkeys ............................................................................. 67

Working with ADKs.................................................................................. 72

Working with Revokers............................................................................ 74

Splitting and Rejoining Keys.....................................................................75

If You Lost Your Key or Passphrase ........................................................78

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

Examining and Setting Key Properties

The PGP Keys Work Area can display these important details about your keys:

 Name

 Email address

PGP® Desktop for Windows Managing PGP Keys

 Validity

 Size

 KeyID

 Trust

 Creation date

 Expiration date

 ADK

 Status

 Key description

 Key usage

You can choose how many or how few details are displayed by clicking the

Keys item, then choosing columns to display by selecting View > Columns.

You can, however, see more information about a key and you can modify certain information about a key, by examining its key properties.

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 120).

 To view a key’s properties

1 Open PGP Desktop, click the PGP Keys Control box, and then click All Keys

in the Control box. All keys on your keyring appear.

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

Properties dialog box for the key you selected is displayed.

PGP® Desktop for Windows Managing PGP Keys

Working With Photographic IDs

You can include a photographic ID on your Diffie-Hellman/DSS and RSA keys.

 To add your photograph to your key

1 Open PGP Desktop, click the PGP Keys Control box, and select My Private

Keys.

2 In the PGP Keys Work area, double-click the private key to which you are

adding the photo ID. The Key Properties dialog box for the selected key is displayed.

3 Right-click the placeholder key and silhouette icon and select Add Photo

ID. The Add Photo dialog box is displayed.

4 Drag or paste your photograph onto the Add Photo dialog box or browse to

it by clicking Select File.

5 Click OK. The Passphrase dialog box opens.

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

photo ID is added to your public key.

 To delete a photo ID

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

Remove Photo ID. 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 or address to your key

1 Open PGP Desktop, click the PGP Keys Control box, and select My Private

Keys.

PGP® Desktop for Windows Managing PGP Keys

2 In the PGP Keys Work area, double-click the private key to which you are

adding a user name or email address. The Key Properties dialog box for the key you double-clicked is displayed.

3 Click Add Email Address. The PGP New User Name dialog box is

displayed.

4 Type the new name and email address in the appropriate fields, then click

OK. The PGP Enter Passphrase for Key dialog box is displayed.

5 Enter the private key passphrase of the key you are modifying, then click

OK.

6 To set the new user name and address as the primary identifier for your

key, click the name of the current primary keyholder in the Key Properties dialog box and select the user you just added.

7 Exit the Key Properties dialog box. In the list of keys in PGP Desktop, the

new name is added to the end of the user name list associated with the key.

 To change the primary name associated with your key

1 Do one of the following:

 In the Key Properties dialog box, click the name of the current primary

keyholder and select the name of the user from the list that is displayed.

 In PGP Desktop, expand your key in the keys list, right-click the user

name you want to set as the primary identifier, and choose Set as

Primary Name from the shortcut menu.

 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.

PGP® Desktop for Windows Managing PGP Keys

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 provides an Import Certificate Assistant to help you with this task. For more information, see Using the Import Certificate Assistant (on page

59).

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

environment and you imported an X.509 certificate on a token during enrollment (choosing to import the certificate as a PGP key), you must manually enable the Synchronize keyring with tokens and smart cards option. To do this, in PGP Desktop choose Tools > Options and click the Keys tab. This step is required in order for the key to work properly with PGP Whole Disk Encryption.

Using the Import Certificate Assistant

X.509 certificates can be imported into PGP Desktop from files, the Windows Personal Certificate store, or smart cards. Even smart card-based certificates which appear in your Windows Certificate store may be imported. The Import Certificate Assistant guides you through the importation process.

When importing certificates from files, the certificate can only be imported from a file with a PEM, PFX, P7b, or P12 extension.

Notes: When using certificates from the Windows Personal Certificate store,

you may get prompted for your certificate's password or PIN by Windows itself (or the third-party smart card software, if using smart card-based Windows Personal Certificates).

Some operations, such as changing the certificate's password, are not permitted from within PGP Desktop when using certificates from the Windows Personal Certificate store. Use the Windows (or smart card) software for performing such operations.

PGP® Desktop for Windows Managing PGP Keys

 To import a certificate using the Import Certificate Assistant

Before You Begin: Make sure that you know the passphrase for the

certificate that you are importing.

1 Start the Assistant by:

 Selecting File > Open.

 Selecting File > Import Personal Certificates.

 Dragging the file containing the public key into the PGP Keys window

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

environment, and your administrator has defined that you can choose the method to import the certificate, select:

 Onto an existing key—the certificate is added to a key that is already

in your keyring.

 As new PGP key(s)—a new PGP key is created using the imported

certificate.

 As PGP X.509 wrapper key(s)—a new PGP key is created using the

imported certificate. PGP Desktop treats the new key as an X.509 certificate.

3 After you make your selection, click Next. Either the Certificate Passphrase

Entry screen or the PGP Enter Passphrase dialog box displays.

4 Provide the password for the certificate, then click Next.

 If you are importing the certificate using the Onto an existing key

option, the Select Key screen displays. Go to the next step.

 If you are importing the certificate using the As new PGP key(s)

option, the key is generated. Click Finish. The process is complete.

 If you are importing the certificate using the As PGP X.509 wrapper

key(s) option, the Select key(s) dialog box displays. Click to select the

key, click Import, and the PGP X.509 wrapper key is generated. The process is complete.

5 To complete importing the certificate using the Onto an existing key

option, from the Select Key dialog box, select the key onto which you would like to import the certificate, then type the password for the key. Click Next.

6 The Key Generation Progress dialog box is displayed as the certificate is

imported onto the key.

7 Click Finish. The process is complete.

PGP® Desktop for Windows Managing PGP Keys

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

120).

 To change your private key passphrase

1 Open PGP Desktop, click the PGP Keys Control box, and select My Private

Keys.

2 In the PGP Keys work area, double-click the private key for which you are

changing the passphrase. The Key Properties dialog box is displayed.

3 Click Change Passphrase. The PGP Passphrase Assistant is displayed.

4 Enter your current passphrase for the private key, then click Next. The

Create Passphrase dialog box is displayed.

5 Enter your new passphrase in the first text field, and then enter it again in

the Re-Enter Passphrase field to confirm the new passphrase.

To display your keystrokes as you type your passphrase, select the Show

Keystrokes box.

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 304).

6 Click Finish. Your passphrase is changed.

PGP® Desktop for Windows Managing PGP Keys

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, user ID, or signature from your PGP keyring

1 Open PGP Desktop, click the PGP Keys Control box, and then click All Keys

in the Control box. All keys on your keyring appear.

2 Do one of the following:

 To delete a key, right-click on the key, select Delete from the list of

commands displayed, 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 plus sign

on the left side of the key to display the user IDs and signatures. When you see the user ID or signature you wish to delete, right-click it, select Delete from the list of commands displayed, then click OK on the Confirmation dialog. The user ID or signature is deleted.

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 a keypair that is "implicitly trusted." In order to disable a key that has been set to implicitly trust, you must first change the trust status to

None.

 To disable or enable a public key

1 Open PGP Desktop, click the PGP Keys Control box, and then click All Keys

in the Control box. All keys on your keyring appear.

PGP® Desktop for Windows Managing PGP Keys

2 Double-click the public key you want to disable. The Key Properties 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 or sign. You can use a disabled key, however to 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 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.

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, click the PGP Keys Control box, and then click All Keys

in the Control box.

All keys on your keyring appear.

2 Double-click the public key whose fingerprint you want to check. The Key

Properties dialog box for the key you selected is displayed.

PGP® Desktop for Windows Managing PGP Keys

The fingerprint of the key is shown under the name and email address, in either hexadecimal format (10 sets of four characters per set) or word list format (four columns with five unique words per column).

3 Compare the fingerprint on the key with the original fingerprint. If the two

are the same, then you have the real key. If not, then you do not have the real key.

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.

4 If you have a forged key, delete it.

5 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 may also need to be signed.

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

environment, key signing may be disabled.

 To sign someone’s key

1 Open PGP Desktop, click the PGP Keys Control box, and then click All Keys

in the Control box. All keys on your keyring appear.

2 Do one of the following:

 From the Keys menu, select Sign.

 Right-click on the key you want to sign and select Sign from the list of

The PGP Sign Key dialog box is displayed with the user name/email address and hexadecimal fingerprint displayed in the text box.

commands that is displayed.

3 Select the Allow signature to be exported checkbox, to allow your

signature to be exported with this key.

PGP® Desktop for Windows Managing PGP Keys

An exportable signature is one that is allowed to be sent to servers and travels with the key whenever it is exported, such as by dragging it to an email message. The checkbox provides a shorthand means of indicating that you want to export your signature so that others can rely on your signature and trust your keys as a result.

4 Click More Choices to configure options such as signature type and

signature expiration.

5 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 selecting 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.

6 The Maximum Trust 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.

7 If you want to limit the trusted introducer’s key validation capabilities to a

single domain, type the domain name in the Domain Restriction text box.

8 In the Expiration field, select Never if you don’t want this signature to

expire or select a date on which it does expire.

9 Click OK. The PGP Enter Passphrase for Key dialog box is displayed.

10 Select the key you want to sign with from the list, then type the passphrase

of the signing key, if required. (If the passphrase is already cached, you don’t need to type it again.)

11 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.

PGP® Desktop for Windows Managing PGP Keys

 To revoke your signature

1 Open PGP Desktop, click the PGP Keys Control box, and then click All Keys

in the Control box. All keys on your keyring appear.

2 Expand the key from which you want to revoke your signature until you see

your signing key.

3 Right-click your signing key and then select Revoke from the list of

commands displayed. The Revoke Signature dialog box is displayed.

4 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 Passphrase for Key dialog box is displayed.

5 Enter your passphrase and click OK. Your signature is revoked from the

key.

Note: If your signature was exportable and you distributed the key with the

exportable signature, you must distribute the key with the revoked signature before others can see the revocation.

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.

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

1 Open PGP Desktop, click the PGP Keys Control box, and then click All Keys

in the Control box. All keys on your keyring appear.

2 Double-click the key for which you are granting trust. The Key Properties

dialog box for the key you selected is displayed.

3 Locate the Trust field.

PGP® Desktop for Windows Managing PGP Keys

4 Click the current setting and select the desired setting from the list.

 If you are granting trust for a public key, you can select None,

Marginal, or Trusted. None means you don’t trust the owner to act

as an introducer, Marginal means you partially trust them, Trusted means you fully trust them.

 If you are granting trust for a keypair, you can select None or Implicit.

Only keypairs that you are importing from backup or from another computer of yours need to have their trust set to Implicit; when you create a keypair, its trust is automatically set to Implicit.

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.

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.

PGP® Desktop for Windows Managing PGP Keys

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

Using Separate Subkeys

Here are some examples of how additional separate subkeys can be useful:

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 check mark in the upper left corner.

PGP® Desktop for Windows Managing PGP Keys

 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.

 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.

Viewing Subkeys

 For older PGP Legacy keypairs, subkeys are not supported.

You can view and change the subkey information on your own keypairs. The subkey information on your keyring’s public keypairs can be viewed, but not changed.

 To view subkeys and subkey properties

1 Open PGP Desktop, click the PGP Keys control box, then click All Keys.

All keys on your Keyring appear.

2 View the properties of a key by doing one of the following:

 Double-clicking the key you want to view.

 Right-clicking on the key, then selecting Key Properties from the

shortcut menu.

 Clicking to select the key in the Keyring, then selecting Keys > Key

Properties.

The Key Properties dialog box for the key you selected is displayed.

3 Click the Subkeys heading in the Key Properties dialog box. The Subkeys

for this key are displayed.

4 To view the properties of a subkey, right-click the subkey you want to view

and select Subkey Properties from the shortcut menu.

PGP® Desktop for Windows 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

1 In the Subkeys section of the Key Properties dialog, click the Add button.

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, choose a key size from 1024 to 4096 bits, or type a

custom key size from 1024 to 4096 bits.

4 In the Start Date field, type a date on which the subkey you are creating

becomes effective or choose a date from the calendar.

17).

5 In the Expiration area, select Never, or select Date and specify a date or

select a date from the calendar. This information controls when the subkey expires.

6 Click OK. The Passphrase dialog box is displayed.

7 Type your passphrase and then click OK. The subkey is created.

To specify how the key can be used (such as only for PGP Messaging), see Specifying Key Usage for Subkeys (on page 70).

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.

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 120).

PGP® Desktop for Windows Managing PGP Keys

 To specify key usage

1 Open PGP Desktop, click the PGP Keys control box, then click All Keys.

All keys on your Keyring appear.

2 View the properties of a key by doing one of the following:

 Double-clicking the key you want to view.

 Right-clicking on the key, then selecting Key Properties from the

shortcut menu.

 Clicking to select the key in the Keyring, then selecting Keys > Key

Properties.

The Key Properties dialog box for the key you selected is displayed.

3 Click the Subkeys heading in the Key Properties dialog box. The Subkeys

for this key are displayed.

4 To view the properties of a subkey, right-click the subkey you want to view

and select Subkey Properties from the shortcut menu.

5 Under the Key Usage section, 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.

PGP® Desktop for Windows Managing PGP Keys

Revoking Subkeys

 To revoke a subkey

1 In the Subkeys section of the Key Properties dialog box, select the subkey

you want to revoke, then click Revoke (above the subkey list). A PGP Warning dialog box is displayed, informing you that once you revoke the subkey, other users will not be able to encrypt data to it.

2 Click Yes to revoke the subkey or click No to cancel. The Passphrase dialog

box is displayed.

3 Type your passphrase, then click OK. The subkey is revoked and the icon

changes.

Removing Subkeys

 To remove a subkey

1 In the Subkeys section of the Key Properties dialog box, select the subkey

you want to remove, then click Remove (above the subkey list). A PGP

Warning dialog is displayed, informing you that once you remove the

subkey, you will not be able to decrypt information encrypted to it.

2 Click Yes to remove the subkey or click No to cancel. 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.

PGP® Desktop for Windows Managing PGP Keys

Adding an ADK to a Keypair

 To add an ADK

1 Open PGP Desktop, click the PGP Keys Control box, and then click My

Private Keys in the Control box. The private keys on your keyring appear.

2 Double-click the key to which you are adding an ADK. The Key Properties

dialog box for the key you selected is displayed.

3 Click the up-arrow to the left of ADK, if applicable (only those keys that

already have at least one ADK already assigned will have the up-arrow). The ADK information for this key is displayed, if configured.

4 Click the plus sign icon on the right side of the ADK section. The Select

Key(s) dialog box is displayed.

5 Select the key you want to use as the ADK, then click OK. A PGP Warning

dialog box is displayed, asking if you are sure you would like to add the selected key as an ADK.

Updating an ADK

 To update an ADK

Removing an ADK

6 Click Yes. The PGP Enter Passphrase for Key dialog box is displayed.

7 Type the passphrase for the key to which you are adding the ADK, then

click OK. A PGP Information dialog box is displayed, telling you the ADK was added to the key.

8 Click OK.

Note: If add an ADK to your key, then those who send you encrypted email

must be able to access the public key portion of the 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.

 To remove an ADK

1 Select the ADK you want to remove from the list of ADKs. The selected

ADK highlights.

PGP® Desktop for Windows Managing PGP Keys

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.

Appointing a Designated Revoker

 To add a designated revoker to your key

1 Open PGP Desktop, click the PGP Keys Control box, and then click My

Private Keys in the Control box. The private keys on your keyring appear.

2 Double-click the key to which you are adding a revoker. The Key Properties

dialog box for the key you selected is displayed.

3 Click the plus sign to the left of Revokers, if applicable (only those keys

that already have at least one revoker configured will have the plus sign). The Revokers information for this key is displayed, if configured.

4 Click the plus sign icon on the right side of the Revokers section. The

Select key(s) dialog box is displayed.

5 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).

6 Click Yes to continue or No to cancel. The PGP Enter Passphrase for Key

dialog box is displayed.

7 Type the passphrase for the keypair to which you are adding the revoker,

then click OK. A PGP Information dialog box is displayed.

PGP® Desktop for Windows Managing PGP Keys

8 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.

Revoking a Key

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, click the PGP Keys Control box, and then click My

Private Keys in the Control box. The private keys on your keyring appear.

2 Right-click the key you want to revoke, then select Revoke from the list of

commands displayed. A PGP Warning dialog box is displayed, asking if you are sure you want to revoke this key.

3 Click Yes to confirm your intent to revoke the selected key or No to cancel.

The PGP Enter Passphrase for Key dialog box is displayed.

4 Type 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.

5 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.

PGP® Desktop for Windows Managing PGP Keys

 To create a split key with multiple shares

1 Open PGP Desktop, click the PGP Keys Control box, and then click My

Private Keys in the Control box. The private keys on your keyring appear.

2 Click on the keypair you want to split. The selected keypair highlights.

3 Select Keys > Share Key > Make Shared. The Shared PGP Key dialog box

is displayed.

4 Add shareholders for the split key by dragging and dropping their keys in

the Shareholder list.

To add a shareholder that does not have a public key, click Add, type the person’s name, then allow the person to type in their passphrase. (The shareholder needs to be physically present in order to type their own passphrase.)

5 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 controls, click the name in the shareholder’s list and then use the arrows to adjust the number of shares.

6 Click Split Key. You are prompted to select a directory in which to store the

7 Select a location to store the key shares, then click OK. The Passphrase

8 Enter the passphrase for the key you want to split, then click OK. A

9 Click Yes to split the key. The key is split and the shares are saved in the

10 Distribute the key shares to the owners, then delete the local copies of the

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.

shares.

screen is displayed.

confirmation dialog box is displayed.

location you specified. Each key share is saved with the shareholder’s name as the file name and an SHF extension.

shares.

Once a key is split among multiple shareholders, attempting to sign or decrypt with it will cause PGP Desktop to automatically attempt to rejoin the key.

PGP® Desktop for Windows Managing PGP Keys

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)

 a network connection

 the IP address or Fully Qualified Domain Name of the computer that is

collecting the key shares

2 Do one of the following:

 To temporarily rejoin the key, at the rejoining computer, use Windows

Explorer to select the file(s) that you want to sign or decrypt with the split key.

Right-click on the file(s) and select Sign or Decrypt from the PGP shortcut menu. The PGP Enter Passphrase for Selected Key screen is displayed with the split key selected.

Click OK to reconstitute the selected key. The Key Share Collection screen is displayed.

 To permanently rejoin the key, right-click the split key and select Key

Properties from the menu displayed.

In the Key Properties dialog box, click Join Key (this button is labeled

Change Passphrase for keys that are not split).

The Passphrase dialog box is displayed.

3 Do one of the following:

PGP® Desktop for Windows Managing PGP Keys

 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 diskette, or a mounted drive. Continue with the next step.

 If you are collecting key shares over the network, click Start

Network. The remote user must start PGP Desktop and select Keys > Share Key > Send Key Share. This starts the process of selecting the

share file, decrypting the share file, selecting an authorization key, unlocking the authorization key, and entering the hostname/IP address of the joining computer.

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 dialog box is displayed. If you have not signed the key that is being used to authenticate the remote system, the key is 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.

4 Click Confirm to accept the share file.

5 Continue collecting key shares until the value for Total Shares Collected

matches the value for Total Shares Needed on the Key Shares Collection screen.

6 Click OK.

 If you elected to temporarily rejoin the key in order to decrypt or sign,

the file is signed or decrypted with the split key and the rejoined key is discarded.

 If you elected to permanently rejoin the key, the key is saved as a fully

rejoined key (and is no longer split).

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.

PGP® Desktop for Windows Managing PGP Keys

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 80).

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 create and answer your security questions.

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?”

PGP® Desktop for Windows Managing PGP Keys

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 PGP Keys Control box and then select your key.

2 Select Keys > Create My PGP Questions. The PGP Security Question

Assistant is displayed.

3 Enter the passphrase for your key and click Next. The Create Security

Question 1 of 5 dialog box is displayed.

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.

If you want to completely customize the question to create your own question, select Enter my own question.

PGP® Desktop for Windows Managing PGP Keys

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.

When you have entered all five questions and answers, the Completing the PGP Security Question Assistant screen is displayed. 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

 To reconstruct your key

1 In PGP Desktop, click the PGP Keys Control box and then select your key.

80).

PGP® Desktop for Windows Managing PGP Keys

2 Select Keys > I Lost My Key. The PGP Passphrase Assistant: Answer

Security Questions dialog box is displayed.

Tip: If the questions displayed are not your questions, click the link for

These are not my questions. The PGP Passphrase Assistant: Select Key to Reconstruct dialog box is displayed. Select the Key ID of the key you want to reconstruct and click Next.

3 Answer three of the five security questions correctly and click Next. The

PGP Passphrase Assistant: Success dialog box is displayed.

4 Click Next. to continue with creating a new passphrase. The PGP

Passphrase Assistant: Create Passphrase dialog box is displayed.

5 Enter and re-enter your 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.

6 Click Finish. Your key has been reconstructed.

PGP® Desktop for Windows Managing PGP Keys

Protecting Your 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.................................................................................. 90

Services and Policies ...............................................................................91

Creating a New Security Policy.............................................................. 101

Working with the Security Policy List ....................................................112

PGP Desktop and SSL ...........................................................................118

Key Modes............................................................................................. 120

Viewing the PGP Log .............................................................................123

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.

For incoming messages, PGP Desktop automatically evaluates all incoming email messages and takes the appropriate actions (described in the following section).

PGP® Desktop for Windows Securing Email Messages

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, to 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

101).

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.

Note: PGP Desktop checks only the default keyring. To send encrypted email

to a recipient whose key is on your local keyring, be sure to import the key to your default keyring.

If you have multiple keyrings, the default keyring is the first keyring listed in the PGP Keys control box. To specify a different default keyring, right-click the keyring in the PGP Keys control box, choose Properties, and select the

Default Keyring checkbox.

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

content of these messages; it simply passes the message along to your email client.

PGP® Desktop for Windows Securing Email Messages

 Message encrypted, but not signed. When PGP Desktop sees a 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.

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.

PGP Desktop User's Guide

Specifications and Main Features

Frequently Asked Questions

User Manual

What's New in PGP Desktop for Windows Version 10.0

What's New in PGP Desktop 10.0

Using this Guide

“Managed” versus “Unmanaged” Users

Conventions Used in This Guide

Who Should Read This Document

About PGP Desktop Licensing

Licensing PGP Desktop for Windows

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

Learning More About Cryptography

Using PGP Desktop for the First Time

Installing PGP Desktop

Before You Install

System Requirements

Citrix and Terminal Services Compatibility

Installing and Configuring PGP Desktop

Installing the Software

Upgrading the Software

Licensing PGP Desktop

Running the Setup Assistant

Uninstalling PGP Desktop

Moving Your PGP Desktop Installation From One Computer to Another

Accessing PGP Desktop Features

The PGP Desktop Main Screen

Using the PGP Tray Icon

Using Shortcut Menus in Windows Explorer

Using the Start Menu

PGP Desktop Notifier alerts

PGP Desktop Notifier for Messaging

PGP Desktop Notifier for Disk features

Enabling or Disabling Notifiers

Viewing the PGP Log

Working with PGP Keys

Viewing Keys

Creating a Keypair

Passwords and Passphrases

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

Copying from a Smart Card Directly to Someone’s Keyring

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

Working With Photographic IDs

Managing User Names and Email Addresses on a Key

Importing Keys and X.509 Certificates

Using the Import Certificate Assistant

Changing Your Passphrase

Deleting Keys, User IDs, and Signatures

Disabling and Enabling Public Keys

Verifying a Public Key

Signing a Public Key

Revoking Your Signature from a Public Key

Granting Trust for Key Validations

Working with Subkeys

Using Separate Subkeys