WatchGuard
®
XCS
Extensible Content Security
v9.0 User Guide
WatchGuard XCS
170, 370, 570, 770, 970, 1170
ii WatchGuard XCS
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www.watchguard.com/support
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ABOUT WATCHGUARD
WatchGuard offers affordable, all-in-one network and content security solutions that
provide defense-in-depth and help meet regulatory compliance requirements. The
WatchGuard XTM line combines firewall, VPN, GAV, IPS, spam blocking and URL
filtering to protect your network from spam, viruses, malware, and intrusions. The new
XCS line offers email and web content security combined with data loss prevention.
WatchGuard extensible solutions scale to offer right-sized security ranging from small
businesses to enterprises with 10,000+ employees. WatchGuard builds simple, reliable,
and robust security appliances featuring fast implementation and comprehensive
management and reporting tools. Enterprises throughout the world rely on our
signature red boxes to maximize security without sacrificing efficiency and
productivity.
For more information, please call 206.613.6600 or visit www.watchguard.com
.
Notice to Users
Information in this guide is subject to change without notice. Companies, names, and data used in examples herein are
fictitious unless otherwise noted. No part of this guide may be reproduced or transmitted in any form or by any means,
electronic or mechanical, for any purpose, without the express written permission of WatchGuard Technologies, Inc.
Document version: 1.1
Guide revision: 3/23/10
Copyright, Trademark, and Patent Information
Copyright © 2010 WatchGuard Technologies, Inc. All rights reserved. All trademarks or trade names mentioned herein, if
any, are the property of their respective owners.
Complete copyright, trademark, patent, and licensing information can be found in the Copyright and Licensing Guide,
available online:
http://www.watchguard.com/help/documentation/
This product is for indoor use only.
User Guide iii
Table of Contents
Chapter 1 About the WatchGuard XCS ..................................................................................................... 1
WatchGuard XCS Overview................................................................................................................................ 1
Firewall-level network and system security ............................................................................................ 1
Message delivery security.............................................................................................................................. 1
Web security ....................................................................................................................................................... 2
Content controls ............................................................................................................................................... 2
Virus and spyware scanning ......................................................................................................................... 2
Outbreak control............................................................................................................................................... 2
Malformed message protection .................................................................................................................. 2
Intercept Anti-Spam......................................................................................................................................... 3
ReputationAuthority........................................................................................................................................ 3
Image spam analysis........................................................................................................................................ 4
Threat prevention ............................................................................................................................................. 4
Trusted and blocked senders list................................................................................................................. 4
Spam quarantine............................................................................................................................................... 4
Secure WebMail................................................................................................................................................. 4
Integrated and external message encryption ........................................................................................ 5
Mail delivery encryption................................................................................................................................. 5
Policy controls.................................................................................................................................................... 5
System management ...................................................................................................................................... 6
Clustering............................................................................................................................................................. 6
Reporting ............................................................................................................................................................ 7
Security Connection......................................................................................................................................... 7
Internationalization.......................................................................................................................................... 7
WatchGuard XCS on the DMZ of a network firewall ............................................................................ 8
WatchGuard XCS on the internal network............................................................................................... 9
Network firewall configuration............................................................................................................. 10
DNS configuration for mail routing..................................................................................................... 11
Outbound mail routing............................................................................................................................ 11
Trusted messages ...................................................................................................................................... 12
Inbound and outbound scanning........................................................................................................ 12
SMTP connection ....................................................................................................................................... 12
Virus and spyware checking................................................................................................................... 13
Malformed message checking .............................................................................................................. 13
Attachment size limits.............................................................................................................................. 13
Attachment control................................................................................................................................... 13
iv WatchGuard XCS
Outbreak control........................................................................................................................................ 13
OCF (Objectionable Content Filter)..................................................................................................... 13
Pattern Filters and Specific Access Patterns..................................................................................... 14
Trusted and Blocked Senders List ........................................................................................................ 14
Content Scanning ...................................................................................................................................... 14
Document Fingerprinting....................................................................................................................... 14
Content Rules .............................................................................................................................................. 14
Encryption .................................................................................................................................................... 14
Anti-Spam processing .............................................................................................................................. 14
Mail mappings............................................................................................................................................. 14
Virtual mappings........................................................................................................................................ 14
Relocated Users .......................................................................................................................................... 15
Mail Aliases ................................................................................................................................................... 15
Mail routing.................................................................................................................................................. 15
Message delivery........................................................................................................................................ 15
Message Processing Order Summary...................................................................................................... 15
SMTP Connection Checks ....................................................................................................................... 15
Message Checks.......................................................................................................................................... 16
Intercept Anti-Spam processing........................................................................................................... 16
Chapter 2 System Administration ........................................................................................................... 19
Connect to the WatchGuard XCS................................................................................................................... 19
Navigate the Main Menu................................................................................................................................... 20
Activity................................................................................................................................................................ 20
Security ............................................................................................................................................................... 21
Configuration ................................................................................................................................................... 22
Administration ................................................................................................................................................. 23
Support............................................................................................................................................................... 24
Console activity screen ................................................................................................................................. 25
Admin Menu ................................................................................................................................................ 25
Repair Menu................................................................................................................................................. 26
Misc Menu..................................................................................................................................................... 26
Configure the Admin User................................................................................................................................ 27
Add additional administrative users........................................................................................................ 28
Admin automatic logout.............................................................................................................................. 30
Admin login lockout ...................................................................................................................................... 30
External Proxy Server.......................................................................................................................................... 32
Feature Display..................................................................................................................................................... 34
Chapter 3 Mail Delivery Settings ............................................................................................................. 35
Network Configuration...................................................................................................................................... 35
Network interface configuration............................................................................................................... 37
Advanced parameters ................................................................................................................................... 38
Transparent mode and bridging............................................................................................................... 39
Support Access ................................................................................................................................................ 40
Network Routing of Virtual Interfaces..................................................................................................... 41
Virtual interfaces and trusts ........................................................................................................................ 42
Subdomain routing via MX lookup .......................................................................................................... 44
Subdomain routing and DNS caching .................................................................................................... 44
LDAP routing .................................................................................................................................................... 44
Add rules for relays......................................................................................................................................... 45
Delivery settings.............................................................................................................................................. 46
Gateway features ....................................................................................................................................... 47
Default mail relay ....................................................................................................................................... 47
User Guide v
Failback mail relay...................................................................................................................................... 47
BCC (Blind carbon copy) all mail........................................................................................................... 48
Annotations and delivery warnings .................................................................................................... 48
Advanced mail delivery options................................................................................................................ 51
Advanced SMTP settings......................................................................................................................... 51
SMTP notification....................................................................................................................................... 52
Received header......................................................................................................................................... 52
Mail Aliases............................................................................................................................................................. 53
Uploading Alias Lists...................................................................................................................................... 53
LDAP aliases ...................................................................................................................................................... 53
Mail Mappings ...................................................................................................................................................... 54
Mail mapping as access control................................................................................................................. 55
LDAP virtual mappings ................................................................................................................................. 57
Configure message archiving..................................................................................................................... 63
Configure content control filters for archiving .................................................................................... 64
Configure pattern filters for use with archiving.............................................................................. 64
Configure OCF for archiving .................................................................................................................. 64
Customizing archive headers using policies.................................................................................... 65
Chapter 4 LDAP Configuration ................................................................................................................ 67
LDAP Overview..................................................................................................................................................... 67
Naming conventions ..................................................................................................................................... 67
LDAP schema.................................................................................................................................................... 68
LDAP components.......................................................................................................................................... 68
Clients............................................................................................................................................................. 68
Protocol ......................................................................................................................................................... 69
Operations.................................................................................................................................................... 69
Client session operations ........................................................................................................................ 69
Query operations ....................................................................................................................................... 69
Modification operations .......................................................................................................................... 70
Extended operations ................................................................................................................................ 70
Security .......................................................................................................................................................... 70
Directory Servers.................................................................................................................................................. 71
Testing LDAP servers ..................................................................................................................................... 72
Searching the LDAP tree.......................................................................................................................... 73
Import settings................................................................................................................................................. 77
Mirror LDAP accounts as local users ........................................................................................................ 78
Testing directory users.................................................................................................................................. 78
Cannot contact the LDAP server ............................................................................................................... 88
LDAP user and group imports are failing............................................................................................... 88
Mirror accounts are not created ................................................................................................................ 88
LDAP authentication failures...................................................................................................................... 89
Chapter 5 Message Security ..................................................................................................................... 91
SMTP Mail Access................................................................................................................................................. 91
Anti-Virus ................................................................................................................................................................ 95
Updating pattern files ................................................................................................................................... 97
Spyware Detection.............................................................................................................................................. 98
Configuring spyware detection in a policy....................................................................................... 99
How message encryption works ............................................................................................................ 105
Encryption configuration on the WatchGuard XCS......................................................................... 106
About Token files ......................................................................................................................................... 107
Encryption with Pattern Filters ............................................................................................................... 108
Encryption with the Objectionable Content Filter (OCF) .............................................................. 108
vi WatchGuard XCS
Manage accounts.................................................................................................................................... 110
Managing images ................................................................................................................................... 111
Managing users ....................................................................................................................................... 111
Generate message activity reports................................................................................................... 112
Manage secure messages .................................................................................................................... 112
Read encrypted messages................................................................................................................... 113
Track encrypted messages .................................................................................................................. 114
External Email Message Encryption ........................................................................................................... 115
Configure the encryption server ............................................................................................................ 115
Define mail routes for encryption and decryption .......................................................................... 116
Enable encryption and decryption on the WatchGuard XCS....................................................... 116
Define filter rules for encryption ............................................................................................................ 117
TLS and message history........................................................................................................................... 120
Chapter 6 Content Control .....................................................................................................................123
Attachment Control......................................................................................................................................... 123
Attachment stripping................................................................................................................................. 123
Attachment stripping and DomainKeys signatures........................................................................ 124
Configuring attachment control ............................................................................................................ 124
Editing attachment types.......................................................................................................................... 125
Attachment size limits................................................................................................................................ 126
Attachment size reports ....................................................................................................................... 127
Unopenable attachments......................................................................................................................... 128
Configuring content scanning................................................................................................................ 128
Using pattern filters for content scanning.......................................................................................... 129
Using a policy compliance dictionary for content scanning........................................................ 129
Uploading training documents .............................................................................................................. 133
Configuring Document Fingerprinting................................................................................................ 135
Document Fingerprinting and policies................................................................................................ 136
Reports............................................................................................................................................................. 136
Message history............................................................................................................................................ 136
Email message structure ........................................................................................................................... 137
Message envelope.................................................................................................................................. 138
Message header....................................................................................................................................... 138
Message body .......................................................................................................................................... 138
Message attachment ............................................................................................................................. 138
Credit card pattern filters .......................................................................................................................... 139
Configuring pattern filters........................................................................................................................ 140
Pattern filter preferences .......................................................................................................................... 144
Rerouting mail using pattern filters ...................................................................................................... 145
Configuring content rules......................................................................................................................... 146
Rule ordering................................................................................................................................................. 149
Downloading and uploading content rules....................................................................................... 149
Reporting ........................................................................................................................................................ 151
Message history............................................................................................................................................ 151
Connection rules .......................................................................................................................................... 152
Rule ordering............................................................................................................................................ 154
Reporting ................................................................................................................................................... 154
Character set support................................................................................................................................. 155
Adding a dictionary..................................................................................................................................... 157
Financial and medical dictionaries ........................................................................................................ 158
Weighted dictionaries ................................................................................................................................ 159
Negative dictionary weights............................................................................................................... 160
User Guide vii
Using weighted dictionaries.................................................................................................................... 160
Chapter 7 Intercept Anti-Spam ..............................................................................................................163
Intercept Anti-Spam Overview .................................................................................................................... 163
Trusted and Untrusted Mail Sources ......................................................................................................... 164
Trusted subnet.............................................................................................................................................. 165
Trusting via specific access patterns..................................................................................................... 165
Intercept connection control aggressiveness ................................................................................... 166
Intercept Anti-Spam aggressiveness .................................................................................................... 167
Intercept Anti-Virus aggressiveness...................................................................................................... 167
Intercept Connection Control...................................................................................................................... 168
ReputationAuthority, DNSBL, and Backscatter rejects................................................................... 169
Intercept actions .......................................................................................................................................... 170
Anti-Spam header........................................................................................................................................ 171
ReputationAuthority/DNSBL/UBL timeout setting.......................................................................... 172
Adding a spam words dictionary ........................................................................................................... 175
Mail Anomalies .................................................................................................................................................. 176
DNSBL servers ............................................................................................................................................... 180
Timeout mode............................................................................................................................................... 180
Timeout mode............................................................................................................................................... 182
UBL whitelist.................................................................................................................................................. 182
ReputationAuthority........................................................................................................................................ 183
Domain and sender reputation .............................................................................................................. 183
ReputationAuthority statistics sharing ................................................................................................ 184
Trusted clients and known mail servers .............................................................................................. 185
Configuring ReputationAuthority checks........................................................................................... 186
How Token Analysis works ....................................................................................................................... 190
Token Analysis training.............................................................................................................................. 190
Configuring Token Analysis ..................................................................................................................... 191
Database and Training.......................................................................................................................... 191
Token Analysis advanced options ......................................................................................................... 192
Neutral words........................................................................................................................................... 192
Token Analysis and languages........................................................................................................... 192
Japanese, Chinese, and Korean languages.................................................................................... 193
Image analysis.......................................................................................................................................... 193
PDF spam analysis .................................................................................................................................. 193
Diagnostics................................................................................................................................................ 194
Spam training ........................................................................................................................................... 196
Spam settings........................................................................................................................................... 196
Dictionary spam count.......................................................................................................................... 197
Troubleshooting Token Analysis....................................................................................................... 197
Anti-Spam header........................................................................................................................................ 199
Configuring Backscatter detection........................................................................................................ 200
Sender Policy Framework (SPF)................................................................................................................... 201
SPF records..................................................................................................................................................... 201
Configuring SPF............................................................................................................................................ 202
DomainKeys........................................................................................................................................................ 202
Configuring DomainKeys.......................................................................................................................... 203
DomainKeys log messages....................................................................................................................... 203
DomainKeys outbound message signing........................................................................................... 204
DomainKeys DNS record ...................................................................................................................... 206
Recommended strategy............................................................................................................................ 208
Chapter 8 Web Scanning ........................................................................................................................ 211
viii WatchGuard XCS
Web Scanning Overview................................................................................................................................ 211
Web Content Inspection ........................................................................................................................... 211
Web Proxy authentication........................................................................................................................ 212
Single sign-on IP address-based authentication......................................................................... 212
Single sign-on IP address and portal authentication notes .................................................... 212
TrafficAccelerator......................................................................................................................................... 212
Web Proxy chaining .................................................................................................................................... 213
Automatic client web proxy configuration ........................................................................................ 213
Web Proxy best practices.......................................................................................................................... 213
Deployment........................................................................................................................................................ 214
Full proxy parallel deployment............................................................................................................... 214
Disadvantages.......................................................................................................................................... 215
Internal network deployment ................................................................................................................. 215
Advantages ............................................................................................................................................... 215
Disadvantages.......................................................................................................................................... 215
Advantages ............................................................................................................................................... 216
Disadvantages.......................................................................................................................................... 216
Transparent Mode ............................................................................................................................................ 219
Disabling the Web Proxy in Transparent Mode ........................................................................... 220
Web Proxy network interface settings ................................................................................................. 220
Configuring LDAP Web User authentication ..................................................................................... 221
Enabling web proxy authentication...................................................................................................... 222
Web Proxy authentication logout.......................................................................................................... 223
Web Cache .......................................................................................................................................................... 224
Web cache disk usage ................................................................................................................................ 225
Flushing the web cache............................................................................................................................. 225
Flush domain web cache .......................................................................................................................... 226
Web streaming Media Bypass...................................................................................................................... 226
Configuring skipped MIME types........................................................................................................... 227
IP authentication browser configuration mode ............................................................................... 228
PAC file........................................................................................................................................................ 229
Load balancing via URL address........................................................................................................ 230
Bypassing the proxy for specific URLs/domains.......................................................................... 231
WPAD using DNS..................................................................................................................................... 231
WPAD using DHCP.................................................................................................................................. 231
Internet Explorer client configuration............................................................................................. 232
Client browser notifications..................................................................................................................... 233
Create a trusted or blocked sites list ................................................................................................ 235
Configure trusted and blocked sites lists ....................................................................................... 235
Web Proxy URL and IP address blocking ........................................................................................ 236
Default blocked categories.................................................................................................................. 241
Categories to block if required by an organization .................................................................... 241
Categories to block to enhance productivity ............................................................................... 242
Configuring URL Categorization ............................................................................................................ 242
Control list updates..................................................................................................................................... 243
Using URL categorization in policies .................................................................................................... 243
URL reject categorization.......................................................................................................................... 244
Chapter 9 User Accounts ........................................................................................................................245
Local User Accounts......................................................................................................................................... 245
Upload and download user lists............................................................................................................. 246
Tiered Administration ..................................................................................................................................... 246
Tiered Admin and WebMail access........................................................................................................ 248
User Guide ix
Log in with Tiered Admin privileges..................................................................................................... 248
Delegated Domain Administration............................................................................................................ 249
Delegated domain administration and clustering .......................................................................... 249
Creating delegated domains................................................................................................................... 250
Deleting a delegated domain.................................................................................................................. 251
Uploading delegated domains ............................................................................................................... 251
Uploaded delegated domain admin users......................................................................................... 252
Delegated domain policies ...................................................................................................................... 253
Administering delegated domains........................................................................................................ 253
Log in to delegated domain administration...................................................................................... 254
Managing the delegated domain.......................................................................................................... 254
Viewing the delegated domain quarantine....................................................................................... 254
Mirror Accounts................................................................................................................................................. 255
CRYPTOCard................................................................................................................................................... 256
SafeWord......................................................................................................................................................... 256
SecurID............................................................................................................................................................. 256
Remote Accounts and Directory Authentication.................................................................................. 257
Configuring LDAP authentication ......................................................................................................... 257
RADIUS authentication .............................................................................................................................. 258
POP3 and IMAP Access ................................................................................................................................... 259
Relocated Users................................................................................................................................................. 260
Vacation Notification....................................................................................................................................... 260
User vacation notification profile........................................................................................................... 261
Chapter 10 Spam Quarantine and Trusted/Blocked Senders ...............................................................263
User Spam Quarantine.................................................................................................................................... 263
Local Spam Quarantine account ............................................................................................................ 263
Configure the Spam Quarantine ............................................................................................................ 264
Spam summary message .......................................................................................................................... 265
Accessing quarantined spam .................................................................................................................. 266
Accessing the quarantine folder via IMAP.......................................................................................... 266
Trusted Senders List.................................................................................................................................... 269
Blocked Senders List ................................................................................................................................... 269
Import list file............................................................................................................................................ 272
Chapter 11 Secure WebMail ..................................................................................................................... 275
Secure WebMail Overview............................................................................................................................. 275
Configure Secure WebMail....................................................................................................................... 276
Enable the Secure WebMail OWA proxy.............................................................................................. 279
Exchange Authentication ......................................................................................................................... 282
Configuring WebMail client options..................................................................................................... 288
Chapter 12 Policies ................................................................................................................................... 289
Policy Overview................................................................................................................................................. 289
Policy hierarchy ............................................................................................................................................ 290
Multiple group policies......................................................................................................................... 290
Pattern filter priority............................................................................................................................... 291
Define global settings ................................................................................................................................ 292
Configure the Default policy.................................................................................................................... 292
Anti-Spam and Anti-Virus .................................................................................................................... 293
Content Control policy settings......................................................................................................... 294
Email policy options............................................................................................................................... 295
HTTP policy options ............................................................................................................................... 296
Add and define domain, group, and user policies........................................................................... 297
x WatchGuard XCS
Uploading and downloading domain policy lists............................................................................ 299
Enabling Group Policy................................................................................................................................ 300
Importing LDAP group information...................................................................................................... 301
Re-Ordering groups .................................................................................................................................... 302
Assigning group policies........................................................................................................................... 303
Uploading group policy lists.................................................................................................................... 303
Orphaned groups......................................................................................................................................... 303
Policy Diagnostics............................................................................................................................................. 305
Chapter 13 Threat Prevention ................................................................................................................. 307
Threat Prevention Overview......................................................................................................................... 307
How Threat Prevention works................................................................................................................. 307
Threat Prevention in a cluster.................................................................................................................. 308
Configure Threat Prevention........................................................................................................................ 308
Basic rule structure ...................................................................................................................................... 311
Default connection rules........................................................................................................................... 311
Blacklisted clients.................................................................................................................................... 311
Directory harvesters............................................................................................................................... 312
Big virus senders...................................................................................................................................... 312
DNSBL clients (on more than one list)............................................................................................. 312
Junk senders ............................................................................................................................................. 313
Internal DoS............................................................................................................................................... 313
Excessive senders.................................................................................................................................... 314
Create connection rules............................................................................................................................. 314
Build condition statements...................................................................................................................... 315
General statistics ..................................................................................................................................... 315
Email Statistics.......................................................................................................................................... 316
Connection rules script error checking................................................................................................ 318
Uploading and downloading addresses ............................................................................................. 320
Integration with F5 and Cisco devices ................................................................................................. 321
Configuring data groups........................................................................................................................... 321
Configuring F5 data groups..................................................................................................................... 324
WatchGuard XCS and F5 integration notes........................................................................................ 326
Enabling data transfer to a Cisco device ............................................................................................. 327
Cisco device configuration....................................................................................................................... 328
Chapter 14 Clustering ...............................................................................................................................331
Clustering Overview ........................................................................................................................................ 331
Cluster architecture..................................................................................................................................... 331
Load balancing ............................................................................................................................................. 332
Email load balancing via DNS............................................................................................................. 332
Traffic load balancing using a load balancing device................................................................ 333
Configure Clustering ....................................................................................................................................... 333
Hardware and licensing............................................................................................................................. 333
Cluster network configuration................................................................................................................ 333
Select a cluster mode ................................................................................................................................. 334
Cluster Management....................................................................................................................................... 335
Cluster activity............................................................................................................................................... 335
HTTP statistics........................................................................................................................................... 336
Stop and start messaging queues ................................................................................................
......... 337
Changing cluster run modes ................................................................................................................... 337
Cluster system maintenance.................................................................................................................... 338
Updating cluster systems..................................................................................................................... 338
Cluster reporting and message history................................................................................................ 338
User Guide xi
Cluster system failures ............................................................................................................................... 338
Backup and restore in a cluster............................................................................................................... 339
Recovering a primary cluster system............................................................................................... 339
Recovering a Secondary and Client cluster system.................................................................... 339
Threat prevention and clustering .......................................................................................................... 339
Clustering and centralized management ........................................................................................... 339
Chapter 15 Centralized Management ..................................................................................................... 341
About Centralized Management ................................................................................................................ 341
Centralized Management and Clustering........................................................................................... 342
Centralized Management features........................................................................................................ 342
Centralized Management in a Cluster.................................................................................................. 343
Networking ports and addresses ........................................................................................................... 344
Create a Centralized Management Federation...................................................................................... 345
Enable Centralized Management on the Manager system .......................................................... 345
Configure Manager Systems in a Cluster ............................................................................................ 346
Enable Centralized Management on Entity systems ...................................................................... 348
Adding Entities to a Federation via the Manager system ............................................................. 349
Configuration Set Features....................................................................................................................... 351
Create a configuration set ........................................................................................................................ 353
Define a configuration set ........................................................................................................................ 354
Apply a configuration set.......................................................................................................................... 355
Viewing a configuration set on an Entity ............................................................................................ 355
Purge local settings ................................................................................................................................ 356
Entity Status ................................................................................................................................................... 357
Centralized Management Reports.............................................................................................................. 358
Viewing Centralized Management reports ........................................................................................ 358
Chapter 16 Reports and Logs ...................................................................................................................361
Reports Overview ............................................................................................................................................. 361
Domain reporting ........................................................................................................................................ 362
Inbound and outbound reporting......................................................................................................... 362
Scheduling reports ...................................................................................................................................... 362
Create a new report..................................................................................................................................... 363
Domain reporting ................................................................................................................................... 364
View reports................................................................................................................................................... 365
Configure Reports ............................................................................................................................................ 371
Spam logging................................................................................................................................................ 372
Searching the mail logs ............................................................................................................................. 374
Searching the system log.......................................................................................................................... 375
WatchGuard XCS Logs .................................................................................................................................... 376
Previous Searches............................................................................................................................................. 377
Log search configuration .......................................................................................................................... 379
Chapter 17 System Management ............................................................................................................ 381
Backup and Restore ......................................................................................................................................... 381
Restore from backup.............................................................................................................................. 381
Backup file naming conventions............................................................................................................ 382
Starting a backup......................................................................................................................................... 382
FTP backup options................................................................................................................................ 383
SCP backup options ............................................................................................................................... 384
Local disk options ................................................................................................................................... 385
Restoring from backup .............................................................................................................................. 386
FTP restore options ................................................................................................................................ 386
xii WatchGuard XCS
Restore from SCP..................................................................................................................................... 387
Restore from local disk.......................................................................................................................... 388
Backup and restore errors......................................................................................................................... 389
Reset the WatchGuard XCS ........................................................................................................................... 390
Get a feature key from LiveSecurity ...................................................................................................... 392
Adding a feature key to your WatchGuard XCS................................................................................ 393
Updating a feature key .............................................................................................................................. 394
Removing a feature key............................................................................................................................. 395
Feature key expiration ............................................................................................................................... 395
Selecting performance settings.............................................................................................................. 400
Chapter 18 Monitor your WatchGuard XCS ............................................................................................405
Dashboard........................................................................................................................................................... 405
Mail summary................................................................................................................................................ 406
Mail resources........................................................................................................................................... 406
Mail traffic summary .............................................................................................................................. 407
Web traffic ................................................................................................................................................. 409
Recent web activity..................................................................................................................................... 411
Status and actions........................................................................................................................................ 412
System status................................................................................................................................................. 415
Diagnostics..................................................................................................................................................... 417
Current admin and WebMail users........................................................................................................ 417
Configuration information ....................................................................................................................... 417
Quarantine expiry options........................................................................................................................ 420
Advanced search.......................................................................................................................................... 423
Message history search tips ..................................................................................................................... 424
System history.................................................................................................................................................... 424
Configure SNMP ........................................................................................................................................... 430
Permitted clients .......................................................................................................................................... 430
MIB files............................................................................................................................................................ 431
Alarms in a cluster........................................................................................................................................ 433
Configuring alarms...................................................................................................................................... 433
Alarms list........................................................................................................................................................ 434
Chapter 19 Troubleshoot your WatchGuard XCS ...................................................................................435
Troubleshoot Message Delivery.................................................................................................................. 435
Troubleshooting Tools.................................................................................................................................... 436
Monitoring the Dashboard....................................................................................................................... 436
Examine Log Files ............................................................................................................................................. 438
Flush mail queue.......................................................................................................................................... 439
Flush DNS cache........................................................................................................................................... 439
Flush web cache........................................................................................................................................... 439
Flush domain web cache .......................................................................................................................... 439
Policy trace ..................................................................................................................................................... 440
Flush web single sign-on sessions......................................................................................................... 440
Hostname lookup ........................................................................................................................................ 440
SMTP probe.................................................................................................................................................... 441
Message history............................................................................................................................................ 445
User Guide 1
1
About the WatchGuard XCS
WatchGuard XCS Overview
The WatchGuard XCS is the industry’s first consolidated messaging security platform delivering integrated
protection, control, and management for email and web content.
Firewall-level network and system security
The WatchGuard XCS delivers the most complete security available for messaging systems. The system runs
on a customized and hardened Unix operating system, and does not allow uncontrolled access to the system.
There is no command line access and the WatchGuard XCS runs as a closed system, preventing accidental or
deliberate misconfiguration by administrators, which is a common cause of security vulnerabilities.
Message delivery security
The WatchGuard XCS provides content security that enables instant-on data loss prevention, encryption and
content filtering with integrated threat prevention for viruses, spam, spyware, phishing, and malware attacks,
all in a secured appliance. Additionally, the WatchGuard XCS protects outbound content against
unintentional or malicious data loss, privacy discrepancies and non-compliance with regulations and
company policies.
The WatchGuard XCS utilizes a sophisticated message delivery system with several security features and
benefits to ensure that the identifying information about your company’s messaging infrastructure remains
private.
 For a company with multiple domain names, the system can accept, process, and deliver mail to
private email servers. For a company with multiple private email servers, the system can route mail
based on the domain or subdomain to separate groups of email users.
 Security features such as mail mappings and address masquerading allow the ability to hide references
to internal host names.
About the WatchGuard XCS
2 WatchGuard XCS
Web security
The WatchGuard XCS incorporates a Web Proxy that allows the system to proxy web traffic and control access
to external web sites. The system can scan web traffic using a subset of the same scanners that examine email
messages to inspect the content of web traffic and downloaded files. Policy features allow specific HTTP
access policies to be applied to different users, groups, and domains, and notifications for blocked
connections or files can be customized and sent to the administrator and recipient.
The Web TrafficAccelerator solution provides critical Web traffic enhancements, such as disk caching and
streaming media support that reduce bandwidth consumption, server loads and latency to improve network
performance.
Content controls
The WatchGuard XCS implements attachment control, content scanning, and content filtering based on
pattern and text matching. These content controls prevent the following issues:
 Breaches of confidentiality
 Legal liability from offensive content
 Personal abuse of company resources
 Breaches of compliance policies
Attachment controls are based on the following characteristics:
 File Extension Suffix — The suffix of the file is checked to determine the attachment type, such as
.exe, or .jpg.
 MIME Content Type — MIME (Multipurpose Internet Mail Extensions) can be used to identify the
actual content type of the message.
 Content Analysis — The file is analyzed to look for characteristics that can identify the file type. This
analysis ensures that the attachment controls are not circumvented by simply renaming a file.
 Content Scanning — Attachments such as Adobe® PDFs or Microsoft® Word documents can be
analyzed for words or phrases that match a pattern filter or compliance dictionary.
Virus and spyware scanning
The WatchGuard XCS features a virus scanning engine based on Kaspersky® Anti-Virus. Email messages and
Web requests in both inbound and outbound directions can be scanned for viruses and spyware. The high
performance virus scanning provides a vital layer of protection against viruses for your entire organization.
Automatic pattern file updates ensure that the latest viruses and spyware are detected.
Outbreak control
The Outbreak Control feature provides customers with zero-day protection against early virus outbreaks. For
most virus attacks, the time from the moment the virus is released to the time a pattern file is available to
protect against the virus can be several hours. During this period, mail recipients are vulnerable to potential
threats. The Outbreak Control feature can detect and take action against early virus outbreaks to contain the
virus threat.
Malformed message protection
Similar to malformed data packets used to subvert networks, malformed messages allow viruses and other
attacks to avoid detection, crash systems, and lock up mail servers. The system ensures that only correctly
formatted messages are allowed into your mail systems. Message integrity checking protects your mail servers
and clients and improves the effectiveness of existing virus scanning implementations.
User Guide 3
About the WatchGuard XCS
Intercept Anti-Spam
The WatchGuard XCS provides a complete set of Anti-Spam features specifically designed to protect against
the full spectrum of current and evolving spam threats. Intercept can combine the results of several Anti-Spam
components to provide a better informed decision on whether a message is spam or legitimate mail while
minimizing false positives. These features include:
 Spam Words — Filters messages based on a dictionary of typical spam words and phrases that are
matched against a message.
 Mail Anomalies — Checks various aspects of the incoming message for issues such as unauthorized
SMTP pipelining, missing headers, and mismatched identification fields.
 DNS Block List (DNSBL) — Detects spam using domain-based lists of hosts with a poor reputation.
Messages can also be rejected immediately regardless of the results of other anti-spam processing if
the client is listed on a DNSBL. A configurable threshold allows administrators to specify how many
DNSBLs must trigger to consider the sender as unreliable.
 URL Block List — Detects spam by examining the URLs in a message and querying a SURBL (Spam URI
Realtime Block Lists) server to determine if this URL has been used in spam messages.
 ReputationAuthority — The ReputationAuthority helps to identify spam by reporting a collection of
metrics about the sender of a message, including their overall reputation, whether the sender is a dial-
up, and whether the sender appears to be virus-infected, based on information collected from installed
customer products and global DNS Block Lists. This information can be used by Intercept to reject the
message, or used as part of the overall Anti-Spam decision.
 Token Analysis — Detects spam based on advanced content analysis using databases of known spam
and valid mail. This feature is also specially engineered to effectively detect image spam.
 Backscatter Detection — Detects spam based on signature verification of the Envelope Sender to
prevent spam bounce emails to forged sender addresses.
 Sender Policy Framework (SPF) — Performs a check of a sending host’s SPF DNS records to identify
the source of a message.
 DomainKeys Authentication — Performs a check of a sending host’s DomainKeys DNS records to
identify the source of a message.
 Intercept Plug-in for Exchange — To further aid administrators with integrating the WatchGuard XCS
into a Microsoft Exchange environment, the Intercept Plug-in for Exchange is provided. This plug-in is
designed to allow customers the ability to integrate the WatchGuard XCS with their existing Exchange
services by allowing Intercept spam classifications to be translated into equivalent values that are used
by the Exchange server to evaluate and classify spam.
ReputationAuthority
The ReputationAuthority helps to identify spam by reporting behavioral information about the sender of a
message, including their overall reputation, whether the sender is a dial-up, and whether the sender appears
to be virus-infected or sends large amounts of spam messages, based on information collected from installed
customer products and global DNS Block Lists. Domain and Sender Reputation increases the effectiveness of
ReputationAuthority by examining not only the IP reputation of a sender, but also the domain name and
envelope sender information from that IP address. This information can be used by the system to either reject
the message immediately or contribute to the Intercept score if a message is detected from a source with a
poor reputation or numerous virus infections.
About the WatchGuard XCS
4 WatchGuard XCS
If Reputation checks are enabled, the WatchGuard XCS will query the statistics on the ReputationAuthority
Domain service for the sender IP address of each message received, excluding those addresses from trusted
and known networks. Using the information returned from ReputationAuthority, the system can make a
decision about whether a message is spam or legitimate mail. A reputation of 0 indicates the sender is
extremely reliable and rarely sends spam or viruses. A reputation of 100 indicates the sender is extremely
unreliable and often sends spam or viruses. An IP address with no previous information from any source is
assigned a value of 50.
Image spam analysis
An image spam email message typically consists of random text or no text body and contains an attachment
picture (usually .gif or .jpg format) that supplies the text and graphics of the spam message. These types of
spam messages are difficult to detect because the message contains no helpful text or URL characteristics that
can be scanned and analyzed. The Image Spam Analysis feature performs advanced analysis of image
attachments to help determine if the message is spam or legitimate mail. Similar to the other anti-spam
features that detect spam characteristics in the text of a message, the Image Spam Analysis feature extracts
certain characteristics of the attached image to determine if these characteristics are similar to those seen in
actual spam messages.
Threat prevention
Threat Prevention allows organizations to detect and block incoming threats in real-time. Threat types can be
monitored and recorded to track client IP behavior and reputation. By examining message flow patterns, the
system detects whether a sending host is behaving maliciously by sending out viruses, spam, or attempting
denial-of-service (DoS) attacks. By instantly recognizing these types of patterns, Threat Prevention presents an
effective solution against immediate attacks. The Threat Prevention feature can block or throttle inbound
connections before the content is processed to lessen the impact of a large number of inbound messages.
Trusted and blocked senders list
Users can create their own personal Trusted and Blocked Senders Lists based on a sender’s email address. The
Trusted email addresses will be exempt from the system’s spam controls, allowing users to trust legitimate
senders, while email addresses on the Blocked Senders List will be prevented from sending mail to that user
via this WatchGuard XCS.
Spam quarantine
The Spam Quarantine is used to redirect spam mail into a local storage area for each individual user. Users will
be able to connect to the system either directly or through a summary email to view and manage their own
quarantined spam. Messages can be deleted, or moved to the user’s local mail folders. Automatic notifications
can be sent to end users notifying them of the existence of messages in their personal quarantine area. For
large enterprises, a dedicated Quarantine Server can be utilized to support up to 100,000 quarantine users.
Secure WebMail
Secure WebMail provides remote access support to internal mail servers. With Secure WebMail, users can
access their mailboxes using email web clients such as Outlook® Web Access, Lotus iNotes, or the WatchGuard
XCS’s own web mail client. The WatchGuard XCS addresses the security issues currently preventing
deployment of web mail services by providing the following protection:
 Strong authentication (including integration with Active Directory)
 Encrypted sessions
 Advanced session control to prevent information leaks on workstations
User Guide 5
About the WatchGuard XCS
Authentication
The WatchGuard XCS supports the following authentication methods for administrators, WebMail users,
Trusted/Blocked Senders List, and Spam Quarantine purposes:
 User ID and Password
 LDAP
 RADIUS
 RSA SecurID
® tokens
 SafeWord and CRYPTOCard tokens
Integrated and external message encryption
The WatchGuard XCS provides an integrated message encryption option and also provides integration with
external encryption servers to provide email encryption and decryption functionality. Email encryption allows
individual messages to be encrypted by the system’s integrated encryption server or a separate encryption
server before being delivered to their destination by the WatchGuard XCS.
Incoming encrypted messages can also be sent to the encryption server to be decrypted before the
WatchGuard XCS accepts the message and delivers it to the intended recipient. This integration allows
organizations to ensure that encrypted messages are still processed for security issues such as viruses,
malformed mail, and content filtering and scanning.
Mail delivery encryption
All messages delivered to and from the WatchGuard XCS can be encrypted using TLS (Transport Layer
Security). This includes connections to remote systems, local internal mail systems, or internal mail clients.
Encrypted messages are delivered with complete confidentiality both locally and remotely.
TLS encryption can be used for the following:
 Secure mail delivery on the Internet to prevent anyone from viewing email while in transit
 Secure mail delivery across a LAN to prevent malicious users from viewing email other than their own
 Create policies for secure mail delivery to branch offices, remote users and business partners
 Supports TLS/SSL encryption for all user and administrative sessions.
 TLS/SSL is used to encrypt SMTP sessions, effectively preventing eavesdropping and interception
Policy controls
Policy-based controls allow settings for the WatchGuard XCS’s security features, including Annotations, Anti-
Spam, Anti-Virus, and Attachment Control, to be customized and applied based on the group membership,
domain membership, or email address of the recipient. User groups can be imported from an LDAP-based
directory, and then policies can be created to apply customized settings to these groups. For example, you can
set up an Attachment Control Policy to allow your Development group to accept and send executable files
(.exe), while configuring your Attachment Control settings for all your other departments to block this file type
to prevent the spread of viruses among the general users.
About the WatchGuard XCS
6 WatchGuard XCS
Directory Services
The WatchGuard XCS integrates with LDAP (Lightweight Directory Access Protocol) directory services such as
Active Directory, OpenLDAP, and iPlanet, allowing you to perform the following:
 LDAP lookup prior to internal delivery — The system can check for the existence of an internal user
via LDAP before delivering a message. This feature allows you to reject mail to unknown addresses in
relay domains, reducing the number of attempted deliveries of spam messages for non-existent local
addresses. This check can be performed directly to an LDAP server or to a cached directory stored
locally on the system.
 Group/User Imports — An LDAP lookup will determine the group membership of a user when
applying policy-based controls. LDAP users can also be imported and mirrored on the system to be
used for services such as the Spam Quarantine.
 Authentication — LDAP can be used for authenticating Web Proxy access, IMAP access, user mailbox,
and WebMail logins.
 SMTP Relay Authentication — LDAP can be used for authenticating clients for SMTP Relay.
 Mail Routing — LDAP can be used to lookup mail route information for a domain to deliver mail to its
destination server.
System management
The WatchGuard XCS provides a complete range of monitoring and diagnostics tools to monitor the system
and troubleshoot mail delivery issues. Admin sessions can also be encrypted for additional security, while
comprehensive logs record all mail activity.
 Web Browser-based management — The web browser management interface displays a live view of
system activity and traffic flows. The management interface can be configured to display this
information for one or many systems, including systems in a local cluster or systems that are being
centrally managed.
 Dashboard — The WatchGuard XCS system Dashboard provides administrators with a brief statistical
and graphical summary of current inbound and outbound email and web activity, allowing rapid
assessment of the current status of the WatchGuard XCS.
 Enterprise integration with SNMP — Using SNMP (Simple Network Management Protocol), the
system can generate both information and traps to be used by SNMP monitoring tools. This extends
the administrator’s view of the WatchGuard XCS and allows notification of significant system events,
including excessive traffic flows and system failures.
 Alarms — The system can generate system alarms that can automatically notify the administrator via
email and console alerts of a system condition that requires attention.
 Archiving — Archiving support allows organizations to define additional mail handling controls for
inbound and outbound mail. These features are especially important for organizations that must
archive certain types of mail for regulatory compliance or for corporate security policies.
Clustering
The WatchGuard XCS clustering features provide a highly scalable, redundant messaging security
infrastructure that enables two or more systems to act as a single logical unit for processing messages while
providing redundancy and high availability benefits. There is no theoretical limit to the size of the cluster, and
systems can be easily added to the cluster to increase processing and high-availability capabilities. Clustering
ensures that the flow of traffic is not interrupted due to individual system failures. A cluster can be managed
from any single system in the cluster without the need for a separate management console, and all systems in
the cluster can process messages. Any configuration changes, such as Anti-Spam and Policies, will be
propagated to all systems in the cluster.
User Guide 7
About the WatchGuard XCS
Reporting
The WatchGuard XCS reporting functionality provides a comprehensive range of informative reports that can
be generated in PDF (Adobe Portable Document Format), CSV, and HTML format on demand and at scheduled
times. The reports are derived from information written to the systems and message logs that are stored in the
message database. Up to a month's reporting data can be stored and viewed online depending on message
loads for a particular environment. Reports are stored on the system for online viewing, and can also be
emailed automatically to the systems administrator.
In clustered environments, reports will aggregate information for the entire cluster. System and resource
reports will display information for each system in the cluster.
For organizations that support multiple domains, per domain information can be added to the reports
providing the administrator with statistics for each hosted domain. Hosted domain reports can also be
enabled that create separate reports for a specific domain that can be emailed to the administrators of each
hosted domain.
Security Connection
The Security Connection provides an automated software update service that polls WatchGuard’s support
servers for new updates, security alerts, and Anti-Spam database updates. When new information and
updates are received, a notification can be sent to the administrator.
Internationalization
The WatchGuard XCS supports internationalization for annotations, notification messages, and message
database views. For example, if a message is sent to someone who is on vacation and the message used
character set ISO-2022-JP (Japanese), the vacation notification sent back will be in the same character set. The
message history database can also be viewed using international character sets.
The WatchGuard XCS also supports the ISO-8859-1 (Western European Languages) based character set for
dictionary-based content filtering using the Objectionable Content Filter.
About the WatchGuard XCS
8 WatchGuard XCS
WatchGuard XCS Deployments
The WatchGuard XCS is designed to be situated between internal email servers and clients, and external
servers on the Internet so that there are no direct connections between external and internal systems.
The WatchGuard XCS is typically installed in one of three locations:
 On the DMZ (Demilitarized Zone) of a network firewall
 In parallel with a network firewall
 Behind the existing firewall on the internal network
Messaging traffic is redirected from either the external interface of the network firewall or from the external
router to the system. When the message is accepted and processed, the system initiates a connection to the
internal mail servers to deliver the messages.
WatchGuard XCS on the DMZ of a network firewall
The most common deployment strategy for the WatchGuard XCS is to be situated on the DMZ of a network
firewall. This type of deployment prevents any direct connections from the Internet to the internal mail
servers, and makes sure the WatchGuard XCS is located on a secure network behind the firewall.
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