GFI MailSecurity User Guide

GFI MailSecurity 10.1 for Exchange/SMTP User Guide
http://www.gfi.com
Email: info@gfi.com
Document Version: MSEC-UM-EN-1.00.002 Last updated: July 20, 2010
Contents
1 About GFI MailSecurity 1
1.1 Introduction to GFI MailSecurity .................................................................. 1
1.2 Key features of GFI MailSecurity ................................................................ 1
1.3 GFI MailSecurity components ..................................................................... 2
1.4 GFI MailSecurity from a user's perspective ................................................. 3
1.5 Add-ons - GFI MailEssentials...................................................................... 3
2 Installing GFI MailSecurity 5
2.1 Introduction ................................................................................................. 5
2.2 Typical deployment scenarios ..................................................................... 5
2.3 Which installation mode should I use? ........................................................ 9
2.4 Hardware requirements ............................................................................ 10
2.5 Software requirements .............................................................................. 10
2.6 Important installation notes ....................................................................... 11
2.7 Preparing to install GFI MailSecurity on an IIS mail relay server ............... 12
2.8 Preparing to install GFI MailSecurity on your mail server .......................... 19
2.9 Installing GFI MailSecurity ........................................................................ 19
2.10 GFI MailSecurity Post-Installation Wizard ................................................. 23
2.11 Adding GFI MailSecurity to the Windows DEP Exception List ................... 27
2.12 Securing access to the GFI MailSecurity configuration/quarantine ............ 28
2.13 Securing access to the GFI MailSecurity Quarantine RSS feeds .............. 32
2.14 Accessing the GFI MailSecurity Configuration and Quarantine Store........ 34
2.15 Upgrading from GFI MailSecurity 8 to GFI MailSecurity 10.1 .................... 36
2.16 Upgrading from GFI MailSecurity 9 to GFI MailSecurity 10.1 .................... 39
2.17 Quarantine Upgrade tool ........................................................................... 39
3 General settings 41
3.1 Introduction to settings .............................................................................. 41
3.2 Define the administrator‟s email address .................................................. 41
3.3 Configuring proxy server settings for automatic updates ........................... 41
3.4 Adding Local Domains .............................................................................. 43
3.5 SMTP server bindings .............................................................................. 43
3.6 Managing local users in SMTP mode ........................................................ 44
4 Configuring virus checking 47
4.1 Configuring Virus Scanning Engines ......................................................... 47
4.2 AVG configuration ..................................................................................... 48
4.3 Kaspersky configuration ............................................................................ 50
4.4 BitDefender configuration ......................................................................... 51
4.5 McAfee configuration ................................................................................ 52
4.6 Norman configuration ............................................................................... 54
4.7 Virus scanner actions ............................................................................... 55
4.8 Virus scanner updates .............................................................................. 57
4.9 Setting the Virus Scanning Engines scan priority ...................................... 58
4.10 Configuring Virus Scanning optimizations ................................................. 58
4.11 Configuring Information Store Scanning ................................................... 59
5 Configuring Content Filtering 63
5.1 Introduction ............................................................................................... 63
5.2 Creating a Content Filtering rule ............................................................... 63
5.3 Enabling/disabling rules ............................................................................ 70
5.4 Removing content filtering rules ................................................................ 70
5.5 Modifying an existing rule ......................................................................... 70
5.6 Changing the rule priority .......................................................................... 71
6 Configuring Attachment Filtering 73
6.1 Introduction to Attachment Filtering .......................................................... 73
6.2 Creating an Attachment Filtering rule ........................................................ 73
6.3 Removing attachment rules ...................................................................... 78
6.4 Make changes to an existing rule .............................................................. 79
6.5 Enabling/disabling rules ............................................................................ 79
6.6 Changing the rule priority .......................................................................... 79
7 Decompression engine 81
7.1 Introduction to the Decompression engine ................................................ 81
7.2 Configuring the decompression engine filters ........................................... 82
7.3 Configuring decompression filter actions .................................................. 86
7.4 Enable/disable decompression filters ........................................................ 87
8 The Trojan & Executable Scanner 89
8.1 Introduction to the Trojan & Executable Scanner ...................................... 89
8.2 Configuring the Trojan & Executable Scanner .......................................... 89
8.3 Trojan & Executable Scanner updates ...................................................... 91
9 The Email Exploit Engine 95
9.1 Introduction to e-mail exploits ................................................................... 95
9.2 Configuring the Email Exploit Engine ........................................................ 95
9.3 Email Exploit Engine updates ................................................................... 98
10 The HTML Sanitizer 101
10.1 Introduction to the HTML Sanitizer .......................................................... 101
10.2 Configuring the HTML Sanitizer .............................................................. 101
11 Patch Checking 103
11.1 Introduction to Patch Checking ............................................................... 103
11.2 Downloading and installing software patches .......................................... 103
12 Quarantine 105
12.1 Introduction to the Quarantine Store ....................................................... 105
12.2 The Quarantine Store ............................................................................. 105
12.3 Search Folders ....................................................................................... 107
12.4 Approving emails from the Quarantine Store .......................................... 112
12.5 Deleting emails from the Quarantine Store ............................................. 113
12.6 Rescanning emails from the Quarantine Store ........................................ 114
12.7 View the full security threat report of an email ......................................... 115
12.8 Enable email approval via HTML approval forms .................................... 117
12.9 Quarantined mail from the user point of view .......................................... 118
12.10 Enable quarantine RSS feeds ................................................................. 119
12.11 Enable the Directory Harvesting filter on quarantined emails .................. 122
13 Reporting 127
13.1 Introduction to GFI MailSecurity Reporting.............................................. 127
14 Realtime Monitor 137
14.1 About the Realtime Monitor .................................................................... 137
14.2 Monitoring email activity .......................................................................... 137
15 Miscellaneous 139
15.1 Version Information ................................................................................. 139
16 Advanced topics 141
16.1 Customizing the notification templates .................................................... 141
16.2 Setting Virus Scanning API Performance Monitor Counters .................... 144
17 Troubleshooting 148
17.1 Introduction ............................................................................................. 148
17.2 Knowledge Base ..................................................................................... 148
17.3 Web Forum ............................................................................................. 148
17.4 Request technical support ...................................................................... 148
17.5 Build notifications .................................................................................... 148
18 Index 149

1 About GFI MailSecurity

1.1 Introduction to GFI MailSecurity

The need to monitor email messages for dangerous, offensive or confidential content has never been more evident. The most deadly viruses, able to cripple your email system and corporate network in minutes, are being distributed worldwide via email in a matter of hours (for example, the MyDoom worm). Products that perform single vendor anti-virus scanning do not provide sufficient protection. Worse still, email is likely to become the means for installing backdoors (Trojans) and other harmful programs to help potential intruders break into your network. Products restricted to a single anti-virus engine will not protect against email exploits and attacks of this kind.
Your only defense is to install a comprehensive email content checking and anti-virus solution to safeguard your mail server and network. GFI MailSecurity acts as an email firewall and protects you from email viruses, exploits and threats, as well as email attacks targeted at your organization.
GFI MailSecurity is totally transparent to your users and does not require additional user training.

1.2 Key features of GFI MailSecurity

Virus checking using multiple virus engines

GFI MailSecurity scans email for viruses using multiple anti-virus engines. Scanning email at the gateway and at mail server level prevents viruses from entering and/or spreading within your network. Furthermore, you can avoid the embarrassment of sending infected emails to customers as GFI MailSecurity also checks outgoing mail for viruses. GFI MailSecurity includes the industrial strength Norman and BitDefender anti-virus engines that have received various awards. You also have the option to add the AVG, McAfee and Kaspersky anti-virus engines. Multiple anti-virus engines give you a higher level of security since anti-virus engines complement each other and lower the average response time to a virus outbreak. GFI MailSecurity also includes an auto-update facility that allows you to configure the anti-virus engines so that they automatically check and download any available updates without administrator intervention.

Email attachment checking/filtering

GFI MailSecurity's key feature is the ability to check all inbound and outbound email. It can quarantine all email with dangerous attachments, such as *.exe, *.vbs and other files. Such attachments are more likely to carry a virus, worm or email attack. Since email viruses can spread so quickly and cause immense damage, it is best to quarantine such emails before they are distributed to your email users. When GFI MailSecurity quarantines an email, the administrator can review it and then delete or approve the message.
Furthermore, you might choose to quarantine mails carrying *.mp3 or *.mpg files, as these hog bandwidth and can needlessly burden a mail server's disk space.
Installing GFI MailSecurity GFI MailSecurity 10.1 1
The Attachment Checking module has effectively saved thousands of companies from the LoveLetter virus.

Trojan and Executable Scanner

GFI MailSecurity is able to analyze incoming executables and rate the risk­level of an executable through a GFI patented process. Through the Trojan and Executable Scanner, GFI MailSecurity can detect and block potentially dangerous and unknown Trojans before they enter your network.

HTML Sanitizer

The advent of HTML email has made it possible for hackers/virus writers to trigger commands by embedding them in HTML mail. GFI MailSecurity scans the email body parts and any .htm/.html attachments for scripting code, and cleans up the HTML by removing all the scripting code. The HTML Sanitizer thus protects you from potentially malicious HTML email, containing HTML viruses and attacks launched via HTML email.

Decompression filter

The decompression filter is used to decompress and analyze compressed files (archives) attached to emails. This filter is able to check for and block password-protected archives, corrupted archives and recursive archives. Furthermore, this engine can also monitor the size and amount of the files included in an archive. You can configure this filter to quarantine or delete archives that exceed the specified file count or file size.

1.3 GFI MailSecurity components

GFI MailSecurity scan engine

The GFI MailSecurity scan engine analyzes the con tent of all inbound and outbound email. If you install GFI MailSecurity on the Microsoft Exchange machine, it will also scan the information store. If installed on a Microsoft Exchange 2007/2010 machine, GFI MailSecurity will scan the information store only if the Mailbox Server Role is installed. If you install GFI MailSecurity on a Microsoft Exchange 2007/2010 machine with the Hub Transport Server Role, it will also analyze internal email. When GFI MailSecurity quarantines an email, it informs the appropriate supervisor/administrator via Email/RSS feed, depending on the options you configure.

GFI MailSecurity configuration

Through the GFI MailSecurity configuration, you can configure GFI MailSecurity to fit your needs.
2 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 1 - GFI MailSecurity Configuration

1.4 GFI MailSecurity from a user's perspective

GFI MailSecurity is totally transparent to the user. This means that the user will not notice that GFI MailSecurity is active until it blocks an email that triggers a rule, for example, an email that contains a forbidden attachment or a virus.
In the case of a suspicious attachment, GFI MailSecurity will quarantine the email for review by the administrator. Optionally, the recipient will receive a message indicating that the mail is awaiting administrator review. As soon as the administrator approves the email, GFI MailSecurity will forward the email to the recipient.

1.5 Add-ons - GFI MailEssentials

A companion product to GFI MailSecurity is GFI MailEssentials. GFI MailEssentials adds a number of corporate email features to your mail server, notably:
Anti-spam, using a variety of methods including Bayesian analysis
Installing GFI MailSecurity GFI MailSecurity 10.1 3
Email management, including disclaimers, POP3 downloader and server-
based auto replies and more.
For more information, please visit the GFI website at http://www.gfi.com. NOTE: GFI MailEssentials is available at a bundle price if purchased in
combination with GFI MailSecurity.
4 GFI MailSecurity 10.1 Installing GFI MailSecurity

2 Installing GFI MailSecurity

2.1 Introduction

2.2 Typical deployment scenarios

Installing GFI MailSecurity on your mail server

Figure 1 - Installing GFI MailSecurity on your mail server
Edge Server Role Hub Transport Role (and any other Microsoft Exchange 2007/2010 server
roles which are irrelevant to GFI MailSecurity)
Exchange 2007/2010 server roles which are irrelevant to GFI MailSecurity)
Installing GFI MailSecurity GFI MailSecurity 10.1 5

Installing GFI MailSecurity on a mail relay server

Figure 2 - Installing GFI MailSecurity on a mail gateway/relay server
6 GFI MailSecurity 10.1 Installing GFI MailSecurity

Installing GFI MailSecurity in front of your firewall

Figure 3 - Installing GFI MailSecurity on a separate machine on a DMZ
When GFI MailSecurity is not installed on your mail server: You can perform maintenance on your mail server whilst still receiving
email from the Internet.
Fewer resources are used on your mail server. Additional fault tolerance - if anything happens to your mail server, you
can still receive email. This email is then queued on the GFI MailSecurity machine.

Installing GFI MailSecurity on an Active/Passive Cluster

2007/2010 cluster environment is currently not supported.
Installing GFI MailSecurity GFI MailSecurity 10.1 7
On each node, you have to do the following: Install GFI MailSecurity on the node local hard drive.
NOTE: Do not install GFI MailSecurity on the shared drive.
Web Site.
to the Clustered SMTP Virtual Server instance.
1. Using the Cluster Administrator console make Node1 active.
address of the MAILCLUSTER machine.
4. From the Cluster Administrator console, make Node2 active.
MailSecurity WWW virtual directory.
address of the MAILCLUSTER machine.
8 GFI MailSecurity 10.1 Installing GFI MailSecurity
Article 885440.
Base Article 867624.
1. Using the Cluster Administrator console make Node1 active.
2. Uninstall GFI MailSecurity from Node2.
3. Using the Cluster Administrator console make Node2 active.
4. Uninstall GFI MailSecurity from Node1.

Installing GFI MailSecurity on an Active/Active Cluster

2.3 Which installation mode should I use?

Active Directory mode

Installing GFI MailSecurity GFI MailSecurity 10.1 9

SMTP mode

2.4 Hardware requirements

The hardware requirements for GFI MailSecurity are:
Pentium 4 (or equivalent) - 2Ghz 512MB RAM 1.5 GB of physical disk space

2.5 Software requirements

2.5.1 Supported Operating Systems
Windows Server 2008 Standard or Enterprise (x86 or x64) (R1 or R2) Windows Server 2003 Standard or Enterprise (x86 or x64)
Windows 2000 Server/Advanced Server (Service Pack 1 or higher) Windows XP professional Windows Small Business Server 2000 Windows Small Business Server 2003 Windows Small Business Server 2008
2.5.2 Supported Mail Servers
Microsoft Exchange Server 2010, 2007, 2003, 2000 (SP1) Lotus Notes 5.5, 5.0, 4.5, 4 Any SMTP/POP3 mail server
2.5.3 Other components
Microsoft .Net framework 2.0 MSMQ - Microsoft Messaging Queuing Service Internet Information Services (IIS) - SMTP and World Wide Web services Microsoft Data Access Components (MDAC) 2.8
10 GFI MailSecurity 10.1 Installing GFI MailSecurity

2.6 Important installation notes

Windows XP

Windows Server 2008

Web Server (IIS) role ASP.NET Windows Authentication Services Microsoft SMTP Services
For more information, refer to:
http://kbase.gfi.com/showarticle.asp?id=KBID001596

Microsoft Exchange Server 2007/2010

If you are installing on Microsoft Exchange Server 2007/2010, you need to install one of the following roles;
Edge Server Role, Hub Transport Role or, Mail Server and Hub Transport roles.

Windows Small Business Server

Other installation configurations

http://kbase.gfi.com/showarticle.asp?id=KBID001559.
Installing GFI MailSecurity GFI MailSecurity 10.1 11

2.7 Preparing to install GFI MailSecurity on an IIS mail relay server

About Windows 2000/2003 IIS SMTP & World Wide Web services

Step 1: Verify installation of IIS SMTP and WWW services

Step 2: Specify mail relay server name and assign an IP

12 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 2 - Assign an IP address to the mail relay server

Step 3: Configure the SMTP service to relay mail to your mail server

Start by creating a local domain in IIS to route mail:
3. Configure the domain for inbound message relaying as follows: a) Right-click the Domains node, and then click New Domain.
Installing GFI MailSecurity GFI MailSecurity 10.1 13
Screenshot 3 - SMTP Domain Wizard - Selecting domain type
b) Select Remote and then click Next. c) Type the domain name in the Name box and then click Finish. NOTE: Upon installation, GFI MailSecurity will import Local Domains from the
Configure the domain to relay email to your mail server:
3. Click OK.
14 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 4 - Configure the new domain

Step 4: Secure your mail relay server

Screenshot 5 - Relay Restrictions dialog
Installing GFI MailSecurity GFI MailSecurity 10.1 15
Screenshot 6 - Specify machines which may relay email via virtual server
relay email via this server. If you want to look up the IP address of a specific host, click DNS Lookup.
for the computers that you want to relay.
domain. This means that the domain controller will openly relay emails via this server. Please note that this option adds processing overhead, and may reduce SMTP service performance because it includes reverse DNS Lookups to verify the domain name of all IP addresses that try to relay.

Step 5: Configure your mail server to relay email via the Gateway server

If you have Microsoft Exchange Server 4/5/5.5:

16 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 7 - The Microsoft Internet mail connector
machine running GFI MailSecurity.

If you have Microsoft Exchange Server 2000/2003:

1. Start the Exchange System Manager.
Installing GFI MailSecurity GFI MailSecurity 10.1 17

If you have Lotus Notes:

1. Double-click the Address Book in Lotus Notes.
2. Click on Server item to expand its sub-items.
3. Click Domains and then click Add Domains.
6. Save the settings and restart the Lotus Notes server.

If you have an SMTP/POP3 mail server:

1. Start the configuration program of your mail server.
3. Save the new settings and restart your mail server.

Step 6: The MX record of your domain must point to the mail relay server

you. Since the new mail relay server must receive all inbound email first, you must

Verify the MX record of your DNS server as follows:

1. Open the command prompt, type nslookup and press Enter.
2. Type set type=mx and press Enter.
3. Type your mail domain and press Enter.
18 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 8 - Checking the MX record of your domain

Step 7: Test your new mail relay server

http://support.microsoft.com/support/kb/articles/Q153/1/19.asp
Step 8: Install GFI MailSecurity on the mail relay server
MailSecurity section in this chapter.

2.8 Preparing to install GFI MailSecurity on your mail server

2.9 Installing GFI MailSecurity
Before you install GFI MailSecurity, check the points below:
2. Save any pending work and close all open applications on the machine.
To install GFI MailSecurity follow these steps:
Installing GFI MailSecurity GFI MailSecurity 10.1 19
Screenshot 9 - Define if the server has access to all email users in the Active Directory
option to continue installing GFI MailSecurity in Active Directory mode. In
20 GFI MailSecurity 10.1 Installing GFI MailSecurity
this mode, GFI MailSecurity creates user-based rules, for example Attachment Checking rules, based on the list of users available in the Active Directory. This means that the machine on which GFI MailSecurity is being installed must be behind your firewall (for example, Mail Server) and must have access to the Active Directory containing all your email users (i.e., the machine on which GFI MailSecurity is being installed must be part of the Active Directory domain).
access to Active Directory (DMZ) - Select this option to continue
installing GFI MailSecurity in SMTP mode. In this mode, GFI MailSecurity will create user-based rules, for example Attachment Checking rules, based on the list of email users/addresses imported from your mail server. You must select this mode if you are installing GFI MailSecurity on a machine that does not have access to the Active Directory containing the complete list of all your email users. This includes machines on a DMZ or machines that are not part of the Active Directory Domain. However, you can still choose this mode to install GFI MailSecurity on machines that do have access to the Active Directory containing all your email users.
Click Next to proceed with the installation.
Screenshot 10 - Define your SMTP server and GFI MailSecurity virtual folder details.
Installing GFI MailSecurity GFI MailSecurity 10.1 21
server bindings section in this manual.
Click Next to continue the installation.
22 GFI MailSecurity 10.1 Installing GFI MailSecurity
2.10 GFI MailSecurity Post-Installation Wizard
Microsoft Exchange Server 2007/2010 machine. IMPORTANT: You need to complete this wizard for GFI MailSecurity to work
with Microsoft Exchange Server 2007/2010. The GFI MailSecurity installation wizard launches the GFI MailSecurity Post-
Installation Wizard when you click Finish. The GFI MailSecurity Post­Installation Wizard registers GFI MailSecurity with the local installation of Microsoft Exchange Server 2007/2010 so that it can process and scan the emails passing through the server.
To complete the GFI MailSecurity Post-Installation Wizard, follow these steps:
1. Click Next in the welcome page.
Screenshot 11 - GFI MailSecurity Post-Installation Wizard welcome page
Installing GFI MailSecurity GFI MailSecurity 10.1 23
Screenshot 12 - Collecting information from Microsoft Exchange Server 2007/2010
Remove. NOTE: The local domains you add from this page affect the GFI MailSecurity
24 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 13 - Local domains list
4. Click Next to continue.
Installing GFI MailSecurity GFI MailSecurity 10.1 25
Screenshot 14 - Server roles detected and list of components to install.
6. Click Next to install the required GFI MailSecurity components.
Screenshot 15 - Installing the required GFI MailSecurity components
26 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 16 - GFI MailSecurity Post-Installation Wizard finish page
2.11 Adding GFI MailSecurity to the Windows DEP Exception List
To add the GFI executables in the DEP exception list follow these steps:
Installing GFI MailSecurity GFI MailSecurity 10.1 27
2. From the Advanced tab, click Settings under the Performance area.
3. Click the Data Execution Prevention tab.
4. Click Turn on DEP for all programs and services except those I select.
7. Click Apply and OK to apply the changes.
2.12 Securing access to the GFI MailSecurity configuration/quarantine
28 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 17 - GFI MailSecurity SwitchBoard
local host to the trusted sites list section below.
Screenshot 18 - Local host address must be added to trusted sites list
Installing GFI MailSecurity GFI MailSecurity 10.1 29
Screenshot 19 - Configuration / Quarantine store Access Control Lists
can easily drag and drop accounts and groups between the two lists.
8. When ready click OK.
30 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 20 - New SwitchBoard settings successfully applied
11. When the process completes, click OK.

Adding local host to the trusted sites list

1. Click the Control Panel shortcut under the Start menu.
2. From the Control Panel open the Internet Options applet.
Screenshot 21 - Internet properties dialog
Installing GFI MailSecurity GFI MailSecurity 10.1 31
4. Click Sites.
6. Click Add. The local host address is added to the Web sites list.
Screenshot 22 - Trusted sites dialog
7. Click Close.
2.13 Securing access to the GFI MailSecurity Quarantine RSS feeds
32 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 23 - GFI MailSecurity SwitchBoard
Installing GFI MailSecurity GFI MailSecurity 10.1 33
Screenshot 24 - Quarantine RSS feeds Access Control Lists
it from the list, select the check box under the Deny column.
6. When ready click OK.
Screenshot 25 - New SwitchBoard settings successfully applied
9. When the process completes, click OK.
2.14 Accessing the GFI MailSecurity Configuration and Quarantine Store

Accessing the configuration from the GFI MailSecurity machine

34 GFI MailSecurity 10.1 Installing GFI MailSecurity
Screenshot 26 - GFI MailSecurity accessed under local mode only

Accessing the configuration from a remote machine

1. Start Microsoft Internet Explorer.
2. In the address bar, specify the following address: „http://<machine name>/<virtual directory name>‟ to access the configuration
For example:
quarantine store.
Installing GFI MailSecurity GFI MailSecurity 10.1 35
Screenshot 27 - GFI MailSecurity accessed under IIS mode
2.15 Upgrading from GFI MailSecurity 8 to GFI MailSecurity
10.1
This section therefore shows you how to: Replace your current GFI MailSecurity 8 installation with GFI MailSecurity
10.1.
MailSecurity 10.1‟s new configuration database format.
36 GFI MailSecurity 10.1 Installing GFI MailSecurity
1. Uninstall GFI MailSecurity 8.
Microsoft .Net framework 1.1 / 2.0 MSMQ - Microsoft Messaging Queuing Service. Internet Information Services (IIS) - SMTP service and World Wide Web
service.
NOTE: You must stop the following services before going on to the next step:
GFI Content Security Attendant Service GFI Content Security Auto-Updater Service GFI MailSecurity Attendant Service GFI MailSecurity Scan Engine IIS Admin Simple Mail Transfer Protocol (SMTP).
c:\program files\GFI\ContentSecurity\MailSecurity.
Installing GFI MailSecurity GFI MailSecurity 10.1 37
Screenshot 28 - GFI MailSecurity 8 configuration settings migration tool
6. Double-click the msec8upg.exe file.
8. Click Migrate. NOTE: If you click Migrate and the user lookup mode of GFI MailSecurity 8
Screenshot 29 - User lookup mode mismatch.
38 GFI MailSecurity 10.1 Installing GFI MailSecurity
2.16 Upgrading from GFI MailSecurity 9 to GFI MailSecurity
10.1
MailSecurity to version 10.1, you cannot go back to version 9 of the product. If you are currently using GFI MailSecurity 9, you can upgrade your current
http://customers.gfi.com.
To upgrade:

Quarantine Upgrade tool section in this manual.

2.17 Quarantine Upgrade tool
NOTE: The old quarantine data will not be available until imported.
2.17.1 Using the quarantine upgrade tool
Installing GFI MailSecurity GFI MailSecurity 10.1 39
Screenshot 30 - Quarantine upgrade tool
1. Press Start button to start data migration.
2. Press Pause/Continue button to pause or continue data processing.
40 GFI MailSecurity 10.1 Installing GFI MailSecurity

3 General settings

3.1 Introduction to settings

Screenshot 31 - GFI MailSecurity general settings page
3.2 Define the administrator’s email address
3. Click Apply.

3.3 Configuring proxy server settings for automatic updates

General settings GFI MailSecurity 10.1 41
1. Click the Settings node to open the general settings page.
2. Click the Updates tab.
Screenshot 32 - Updates server proxy settings
4. Click Apply.
42 GFI MailSecurity 10.1 General settings

3.4 Adding Local Domains

Screenshot 33 - Local Domains list
1. Click the Settings node to open the general settings page.
4. Click Apply. NOTE: You can use the local domains option if you want to configure local

3.5 SMTP server bindings

installed on a Microsoft Exchange Server 2007/2010 machine.
General settings GFI MailSecurity 10.1 43
Screenshot 34 - Binding GFI MailSecurity to a different SMTP Server
3. Click Apply.

3.6 Managing local users in SMTP mode

44 GFI MailSecurity 10.1 General settings
Screenshot 35 - User Manager

To add a new local user follow these steps:

1. Enter the email address in the Email address box.
2. Click Add.
General settings GFI MailSecurity 10.1 45
Screenshot 36 - Non-local user entered
3. Repeat steps 1 and 2 to add more than one local user.
4. Click Apply.

To remove a local user follow these steps:

1. Select the local user you want to remove from the Local Users list.
2. Click Remove.
3. Repeat steps 1 and 2 to remove more than one local user.
4. Click Apply.
46 GFI MailSecurity 10.1 General settings

4 Configuring virus checking

4.1 Configuring Virus Scanning Engines

Screenshot 37 - Virus Scanning Engines status page
Configuring virus checking GFI MailSecurity 10.1 47
Screenshot 38 - Information Store Scanning will be disabled.
Screenshot 39 - Enable Information Store protection before configuring a Virus Scanning Engine

4.2 AVG configuration

48 GFI MailSecurity 10.1 Configuring virus checking
Screenshot 40 - Anti-virus Scanning Engines: AVG configuration page (General Tab)
To configure the AVG engine:
Information Store Virus Scanning (VSAPI) check box. NOTE: When GFI MailSecurity is installed on a Microsoft Exchange Server
Configuring virus checking GFI MailSecurity 10.1 49

AVG web site

4.3 Kaspersky configuration

Screenshot 41 - Anti-virus Scanning Engines: Kaspersky configuration page (General Tab)
To configure the Kaspersky engine:
50 GFI MailSecurity 10.1 Configuring virus checking
Information Store Virus Scanning (VSAPI) check box. NOTE: When GFI MailSecurity is installed on a Microsoft Exchange Server
scanner updates sections in this chapter.

Kaspersky web site

4.4 BitDefender configuration

Screenshot 42 - Virus Scanning Engines: BitDefender configuration page (General Tab)
To configure the BitDefender engine:
Configuring virus checking GFI MailSecurity 10.1 51
Information Store Virus Scanning (VSAPI) check box. NOTE: When GFI MailSecurity is installed on a Microsoft Exchange Server
ignore macros and only scan emails for viruses.
to quarantine all emails that contain a macro (even if the macro is a genuine one).

BitDefender website

4.5 McAfee configuration

52 GFI MailSecurity 10.1 Configuring virus checking
Screenshot 43 - Virus Scanning Engines: McAfee configuration page (General Tab)

McAfee website

Configuring virus checking GFI MailSecurity 10.1 53

4.6 Norman configuration

Screenshot 44 - Virus Scanning Engines: Norman configuration page

Norman website

54 GFI MailSecurity 10.1 Configuring virus checking

4.7 Virus scanner actions

Screenshot 45 - Virus Scanning Engine: Configuration page (Actions Tab)
2. Choose one of the following options: Quarantine item - Select this option if you want to quarantine all virus-
infected emails detected by this Virus Scanning Engine. You can subsequently review (approve/delete) all the quarantined emails.
by this Virus Scanning Engine.
Configuring virus checking GFI MailSecurity 10.1 55
users when this filter detects a virus.
administrator whenever this virus scanner detects an infected email.
56 GFI MailSecurity 10.1 Configuring virus checking

4.8 Virus scanner updates

Screenshot 46 - Virus Scanning Engines: Configuration page (Updates Tab)
3. From the Downloading options list, select one of the following: Only check for updates - Select this option if you want GFI MailSecurity
to just check and notify the administrator whenever updates are available for this virus scanner. This option will NOT download the available updates.
MailSecurity to check and automatically download any updates available for this virus scanner.
Configuring virus checking GFI MailSecurity 10.1 57

Triggering the virus update manually

4.9 Setting the Virus Scanning Engines scan priority

1. Click the GFI MailSecurity Virus Scanning Engines node.
Screenshot 47 - Virus Scanning Engines: scan priority list
arrows to respectively increase or decrease the priority of the virus scanner. Repeat the same procedure until the virus scanner reaches the desired position in the priority/execution sequence list.
4.10 Configuring Virus Scanning optimizations
58 GFI MailSecurity 10.1 Configuring virus checking
Screenshot 48 - Configure virus scanning optimizations
4.11 Configuring Information Store Scanning
GFI MailSecurity on the Microsoft Exchange machine. NOTE: When GFI MailSecurity is installed on a Microsoft Exchange Server
To configure the Information Store Scanning feature, follow these steps:
1. Click the GFI MailSecurity Information Store Protection node.
Configuring virus checking GFI MailSecurity 10.1 59
Screenshot 49 - Information Store Protection node
Screenshot 50 - All Information Store Virus Scanning Engines have been enabled.
60 GFI MailSecurity 10.1 Configuring virus checking
Screenshot 51 - VSAPI scan settings
5. Select a VSAPI scan method from the following: On-access scanning - New items in the Information Store are scanned
as soon as they are accessed by the email client. This scan method will thus introduce a short delay before the email client can display the contents of a new message.
added to a queue for scanning. When a mail client tries to access an item that is still in the queue, it will be allocated a higher scanning priority so that it is scanned as soon as possible. This is the default and recommended mode of operation, since in general the delay associated with on-access scanning is avoided because new items are added to the queue immediately and are usually scanned before a mail client requests access to the item.
Configuring virus checking GFI MailSecurity 10.1 61

5 Configuring Content Filtering

5.1 Introduction

The Content Filtering feature allows you to set up rules to filter emails containing particular keywords or a combination of keywords in an email. A rule is composed of:
Keywords to block in the email body, subject or attachment Actions to take when a keyword is found The users to which a rule applies.
NOTE: Although this feature can be used as a filter against spam email, it is recommended to use dedicated software to block spam. For more information, refer to:
http://kbase.gfi.com/showarticle.asp?id=KBID003342
Screenshot 52 - Content Filtering page
To configure keyword-blocking rules, navigate to the Content Filtering node from the GFI MailSecurity Configuration. This page allows you to view, create, enable, disable or delete rules.

5.2 Creating a Content Filtering rule

1. Navigate to GFI MailSecurity ► Content Filtering node and click Add Rule….
Configuring Content Filtering GFI MailSecurity 10.1 63
Check inbound emails
Select this option to scan incoming emails
Check outbound emails
Select this option to scan outgoing emails
Screenshot 53 - Content Filtering: General Tab
2. Specify a name for the rule in the Rule name text box.
3. Select which emails to scan.
4. To block emails encrypted using PGP technology, select Block PGP
encrypted emails. NOTE: PGP encryption is a public-key cryptosystem often used to encrypt
emails.
5. Select the Body tab to specify the keywords in the email body to block.
64 GFI MailSecurity 10.1 Configuring Content Filtering
Screenshot 54 - Content Filtering: Body Tab- setting conditions
7. From the Condition entry area, key in keywords to block in the Edit condition box. You can also use conditions AND, OR, AND NOT and OR NOT to use a combinations of keywords.
8. To add the keyword or combination of keywords keyed in, click Add Condition.
NOTE 1: To modify an entry in the Conditions list, select it and make the
required changes in the Condition entry box. Click Update to apply changes.
NOTE 2: To remove an entry from the Conditions list, select it and click Remove.
Configuring Content Filtering GFI MailSecurity 10.1 65
Match whole words only
Block emails when the keywords specified match whole words.
Apply above conditions to attachments
Select this option to apply this rule also to text in attachments. In the Attachment filtering area specify the attachments to apply or exclude from this rule.
Screenshot 55 - Content Filtering: Body Tab- configuring other options
9. From the Options area, configure other settings:
10. Select the Subject tab to specify keywords to block in the email subject.
66 GFI MailSecurity 10.1 Configuring Content Filtering
Screenshot 56 - Content Filtering: Subject Tab
11. Select Enable subject content checking to enable scanning for keywords in the email subject.
12. In the Enter phrase text box, specify keywords to block, and click Add. NOTE: To remove an added keyword, select it from the Phrases box and
click Remove Selected.
13. From the Options area, configure how keywords are matched. Select Match whole words only to block emails where the keywords specified match whole words in the subject.
14. Click the Actions tab to configure what should be done when this rule is triggered.
15. To block an email that matches the rule conditions, select Block attachment and perform this action and select one of the following options:
Configuring Content Filtering GFI MailSecurity 10.1 67
Quarantine email
Stores emails containing the keyword(s) in the Quarantine Store. You can subsequently review (approve/delete) all the quarantined emails. For more information about Quarantine refer to the
Quarantine chapter in this manual.
Delete email
Deletes emails containing the blocked keyword(s).
Move to folder
Moves the email to a folder on disk. Key in the full folder path where to store blocked emails.
Notify administrator
Notify the administrator whenever the rule is triggered.
Notify local user
Notify the email local recipients about the blocked email.
16. You can configure rule to send email notifications to the administrator and/or user whenever an email containing an attachment is blocked. To do this, from the Notification options area select:
17. To log the activity of this rule to a log file, select Log rule occurrence to this file. In the text box specify:
Path and file name to a custom location on disk where to store the log file,
or
The file name only. The log file will be stored in the following default
location:
<GFI MailSecurity installation path>\ContentSecurity\MailSecurity\DebugL ogs\<filename.txt>
18. By default, the rule is applied to all email users. GFI MailSecurity, however, allows you to apply this rule to a custom list of email users. To specify the users to apply this rule to, select Users/Folders tab
68 GFI MailSecurity 10.1 Configuring Content Filtering
Only this list
Apply this rule to a custom list of email users, groups or public folders.
All except this list
Apply this rule to all email users except for the users, groups or public folders specified in the list.
Screenshot 57 - Content Filtering: Users/Folders Tab
19. Specify the users to apply this rule to.
20. To add email users, user groups and/or public folders to the list, click Add.
21. In the User Lookups window, specify the name of the email user/user group or public folder that you wish to add to the list and click Check Names. Matching users, groups or public folders are listed below.
NOTE: You do not need to input the full name of the users, groups or public folder. It is enough to enter part of the name. GFI MailSecurity will list all the names that contain the specified characters. For example, if you input „sco‟,
GFI MailSecurity will return names like „Scott Adams‟ and „Freeman Prescott„,
if they are available.
22. Select the check box next to the name(s) that you want to add to the list and click OK.
NOTE 1: To remove entries from the list, select the user/user group/public folder you want to remove and click Remove.
Configuring Content Filtering GFI MailSecurity 10.1 69
NOTE 2: If no names are included in the list, GFI MailSecurity automatically applies this rule to all email users.
24. Repeat steps 21 to 23 to add all the required users to the list.
25. Click Apply.

5.3 Enabling/disabling rules

Enabled rules are rules that are active and GFI MailSecurity uses them during scanning. Disabled rules are rules that are inactive and are not currently used by GFI MailSecurity during email scanning.
1. Navigate to the GFI MailSecurity ► Content Filtering node.
2. From the Content Filtering page, select the checkbox of the rule(s) to enable or disable.
3. Click Enable Selected or Disable Selected accordingly.

5.4 Removing content filtering rules

Screenshot 58 - Selecting a Content Filtering rule for removal
1. Navigate to the GFI MailSecurity ► Content Filtering node.
2. From the Content Filtering page, select the checkbox of the rule(s) that you want to remove.
3. Click Remove Selected.

5.5 Modifying an existing rule

1. Click the GFI MailSecurity ► Content Filtering node.
2. From the Content Filtering page, click the name of the rule to modify.
3. Perform the required changes in the rule properties and click Apply to apply changes.
70 GFI MailSecurity 10.1 Configuring Content Filtering

5.6 Changing the rule priority

Content Filtering rules are applied in the same order, from top to bottom as they are listed in the Content Filtering page (that is, rule with priority value 1 is checked first). To change the sequence/priority of rules:
1. Navigate to GFI MailSecurity ► Content Filtering.
2. From the Content Filtering page, click the (up) or (down) arrows to respectively increase or decrease the priority of the rule.
3. Repeat step 2 until rules are placed in the desired sequence.
Configuring Content Filtering GFI MailSecurity 10.1 71

6 Configuring Attachment Filtering

6.1 Introduction to Attachment Filtering

Screenshot 59 - Attachment Filtering page

6.2 Creating an Attachment Filtering rule

To create an Attachment Filtering rule:
1. Click the GFI MailSecurity Attachment Filtering node.
2. From the Attachment Filtering page (in the right window), click Add Rule.
Configuring Attachment Filtering GFI MailSecurity 10.1 73
Screenshot 60 - Attachment Filtering: General Tab
4. Decide on the type of attachment blocking required:
Block all - Select this option to block email attachments of any type.  Block this list - Select this option to block ONLY the listed attachment
types.
74 GFI MailSecurity 10.1 Configuring Attachment Filtering
that are not included in the list.
NOTE: To remove an entry from the list, select it and click Remove Selected.
Screenshot 61 - Attachment Filtering: Actions Tab
Configuring Attachment Filtering GFI MailSecurity 10.1 75
the attachment for review by an administrator. For more information, refer to Quarantine chapter in this manual.
completely.
Input the folder name in the box provided underneath this option.
users when this filter blocks an attachment.
notifications to the administrator whenever an email containing an attachment is blocked. The administrator‟s email address is specified during the installation of GFI MailSecurity but can still be changed from the GFI MailSecurity configuration (GFI MailSecurity Settings node General tab). For more information refer to Define the administrator‟s
email address section in this manual.
76 GFI MailSecurity 10.1 Configuring Attachment Filtering
Screenshot 62 - Attachment Filtering: Users/Folders Tab
11. Choose one of the following options: Only this list - Select this option if you want to apply this rule to all email
users/groups or public folders present in the list.
email users, groups or public folders NOT present in the list.
Screenshot 63 - Add users to an attachment Filtering rule
Configuring Attachment Filtering GFI MailSecurity 10.1 77
NOTE: Repeat steps 12 to 15 to add all the users you want to the list. NOTE: To remove entries from the list, select the user/user group/public
folder you want to remove and click Remove. NOTE: If no names are included in the list, GFI MailSecurity will automatically
apply this rule to all the email users in Active Directory/SMTP address list.
16. Click Apply.

6.3 Removing attachment rules

Screenshot 64 - Selecting an attachment Filtering rule for removal
To Remove an Attachment Filtering rule:
1. Click the GFI MailSecurity Attachment Filtering node.
78 GFI MailSecurity 10.1 Configuring Attachment Filtering
3. Click Remove Selected to delete the selected rules.

6.4 Make changes to an existing rule

To modify an existing rule:
1. Click the GFI MailSecurity Attachment Filtering node.

6.5 Enabling/disabling rules

1. Click the GFI MailSecurity Attachment Filtering node.

6.6 Changing the rule priority

1. Click the GFI MailSecurity Attachment Filtering node.
Configuring Attachment Filtering GFI MailSecurity 10.1 79

7 Decompression engine

7.1 Introduction to the Decompression engine

Screenshot 65 - The decompression engine filters list
The following is a list of archive filters included in the decompression engine:
Check password protected archives Check corrupted archives Check for recursive archives Check size of uncompressed files in archives Check for amount of files in archives Scan within archives
Decompression engine GFI MailSecurity 10.1 81

7.2 Configuring the decompression engine filters

Check password protected archives

Screenshot 66 - Configuring password protected archives options
This filter allows you to quarantine or delete emails that contain password­protected archives. To configure this filter:
1. Click the GFI MailSecurity Decompression node.
password-protected archive. The administrator can later review these quarantined emails and approve or delete them accordingly.
password-protected archives.
decompression filter actions section in this chapter.
6. Click Apply.

Check corrupted archives

Check password protected archives.
82 GFI MailSecurity 10.1 Decompression engine

Check for recursive archives

Screenshot 67 - Configuring recursive archives options
To configure this filter:
1. Click the GFI MailSecurity Decompression node.
recursive archives. The administrator can later review these quarantined emails and approve or delete them accordingly.
recursive archives that exceed the specified nesting limit.
Decompression engine GFI MailSecurity 10.1 83
decompression engine filters section in this chapter.
6. Click Apply.

Check size of uncompressed files in archives

Screenshot 68 - Configuring checks for the size of uncompressed files in archives
To configure this filter:
1. Click the GFI MailSecurity Decompression node.
attachments, thus bypassing the anti-virus checking.
these archives. The administrator can later review these quarantined emails and approve or delete them accordingly.
archived files that when un-compressed, exceed the specified size limit.
84 GFI MailSecurity 10.1 Decompression engine
decompression engine filters section in this chapter.
6. Click Apply.

Check for amount of files in archives

Screenshot 69 - Configuring the amount of files in archive check
To configure this filter:
1. Click the GFI MailSecurity Decompression node.
these archives. The administrator can later review these quarantined emails and approve or delete them accordingly.
Decompression engine GFI MailSecurity 10.1 85
archived files that when uncompressed contain more files than the limit specified.
decompression engine filters section in this chapter.
6. Click Apply.

Scan within archives

Configure this option as follows:
1. Click the GFI MailSecurity Decompression node.
2. From the list of filters (in the right window), click on Scan within archives.

7.3 Configuring decompression filter actions

Screenshot 70 - Decompression filter actions
86 GFI MailSecurity 10.1 Decompression engine
2. Click the Actions tab and select any of the following actions:  Notify local user - Select this option if you want to notify the email local
users when the email contains an archive file that infringes a decompression engine rule.
administrator whenever an email containing an archive is quarantined.
3. Click Apply.

7.4 Enable/disable decompression filters

Screenshot 71 - Decompression tool filters list
To enable or disable any of the available decompression filters:
1. Click the GFI MailSecurity Decompression node.
3. Click Enable selected or Disable selected accordingly. NOTE: You can select all check boxes in one go by selecting the check box
next to the Description column heading at the top-left of the list.
Decompression engine GFI MailSecurity 10.1 87

8 The Trojan & Executable Scanner

8.1 Introduction to the Trojan & Executable Scanner

GFI MailSecurity includes an advanced Trojan and Executable Scanner, which is able to analyze and determine the function of an executable file. This scanner can subsequently quarantine any executables that perform suspicious activities (such as a Trojan).

What is a Trojan horse?

The Trojan horse got its name from the old mythical story about how the Greeks gave their enemy a huge wooden horse as a gift during the war. The enemy accepted this gift and brought it into their fortress. During the night, Greek soldiers crept out of the horse and attacked the city.
In computers a Trojan horse is a way of penetrating a victim‟s computer undetected, allowing the attacker unrestricted access to the data stored on that computer. Subsequently the attacker can manipulate the data and can cause great damage to the victim, just like the citizens of Troy.
A Trojan can be a hidden program that runs on your computer without your knowledge. Furthermore, hackers sometimes hide Trojans into legitimate programs that you normally use.

Difference between Trojans and viruses

The difference between Trojans and viruses is that Trojans are often „one-off‟ („tailor made‟) executables, targeted to obtain information from a specific
target (user/system). In general, a hacker deploys a Trojan to create a backdoor on a system, thus gaining unrestricted access to the system. Signature based anti-virus software, are unable to detect one-off Trojans. Indeed any application that only uses signatures to detect malicious software will not be effective in detecting such threats. These include specialized anti­Trojan software. The main reason is that signature based software can only detect known viruses and Trojans. That is why such applications need frequent updates.

How does the Trojan & Executable Scanner work?

GFI MailSecurity is able to rate the risk-level of an executable file by decompiling the executable, and detecting in real time what the executable might do. Subsequently, it compares capabilities of the executable to a database of malicious actions and then rates the risk level of this executable file. With the Trojan & Executable scanner, you can detect and block potentially dangerous, unknown or one-off Trojans before they penetrate your network.

8.2 Configuring the Trojan & Executable Scanner

From the Trojan & Executable Scanner node, you can define the level of security that you require and the actions you want GFI MailSecurity to take on emails containing malicious executable files.

Configuring the security level

The Trojan & Executable Scanner GFI MailSecurity 10.1 89
Screenshot 72 - Trojan and Executable Scanner: General Tab
To configure the Trojan & Executable Scanner:
1. Click the GFI MailSecurity Trojan & Executable Scanner node.
2. From the configuration options (in the right window), select the Enable Trojan & Executable Scanner check box to activate this filter.
3. Specify the emails you want to check for Trojans and other malicious executables by selecting any of the following options:
Check inbound emails - Select this option to scan inbound emails for
Trojans and malicious executable files.
Check outbound emails - Select this option to scan outbound emails for
Trojans and malicious executable files.
4. Choose the required level of security by selecting one of the following options:
High Security - Select this option to quarantine almost all executables. If
the executable file contains any known malicious signature it will get immediately quarantined.
Medium Security - Select this option to quarantines only suspicious
executables. If the executable contains one high-risk signature or a combination of high-risk and low-risk signatures it will be quarantined.
90 GFI MailSecurity 10.1 The Trojan & Executable Scanner
Low Security - Select this option to quarantine all malicious executables.
If the executable contains at least one high-risk signature, it will be immediately quarantined.

Configuring actions

Screenshot 73 - Trojan and Executables Scanner: Actions Tab
5. Click the Actions tab to configure the actions you want GFI MailSecurity to take on emails containing a malicious executable. Select any of the following options:
Notify local user - Select this option if you want to notify the email local
users when this filter detects a malicious executable.
NOTE: If a threat is detected in an outbound email, the recipients will receive the original email with the malicious parts removed. A security notice is attached to the email to inform the recipients what email parts were removed and for what reason. This behavior is always enabled and is not affected by this setting.
Notify administrator - Select this option to send email notifications to the
administrator whenever an email containing malicious executable is quarantined.
Log occurrence to this file - Select this option to log the event whenever
the Trojan & Executable Scanner detects an infected email. In the edit box below, specify either the file name only or the full path to the log file.
6. Click Apply.

8.3 Trojan & Executable Scanner updates

You can configure GFI MailSecurity to download Trojan & Executable Scanner updates automatically or to notify the administrator whenever new updates are available. To configure automatic updates:
The Trojan & Executable Scanner GFI MailSecurity 10.1 91
1. Click the GFI MailSecurity Trojan & Executable Scanner node.
2. Click the Updates tab in the Trojan & Executable Scanner page (in the right window).
3. Select the Automatically check for updates check box to enable the auto-update feature.
4. From the Downloading options list, select one of the following download options:
Only check for updates - Select this option if you want GFI MailSecurity
to just check and notify the administrator whenever updates are available for the Trojan & Executable Scanner. This option will NOT download the available updates.
Check for updates and download - Select this option if you want GFI
MailSecurity to check and automatically download any updates available for the Trojan & Executable Scanner.
5. Specify how often you want GFI MailSecurity to check/download updates for the Trojan & Executable Scanner, by typing an interval in hours.
6. Click Apply.
Screenshot 74 - Trojan and Executable Scanner: Updates tab

Triggering the Trojan & Executable Scanner update manually

92 GFI MailSecurity 10.1 The Trojan & Executable Scanner
To check/download updates for the Trojan & Executable Scanner immediately, click Download updates.
The Trojan & Executable Scanner GFI MailSecurity 10.1 93
Loading...