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Americas Headquarters
Cisco Systems, Inc.
170 West Tasman Drive
San Jose, CA 95134-1706
USA
http://www.cisco.com
Tel:  408 526-4000
800 553-NETS (6387)
Fax:  408 527-0883
Cisco IronPort AsyncOS 7.5 for Email 
Configuration Guide
October 27, 2011
Text Part Number: OL-25136-01
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THE SPECIFICATIONS AND INFORMATION REGARDING THE PRODUCTS IN THIS MANUAL ARE SUBJECT TO CHANGE WITHOUT 
NOTICE. ALL STATEMENTS, INFORMATION, AND RECOMMENDATIONS IN THIS MANUAL ARE BELIEVED TO BE ACCURATE BUT 
ARE PRESENTED WITHOUT WARRANTY OF ANY KIND, EXPRESS OR IMPLIED. USERS MUST TAKE FULL RESPONSIBILITY FOR 
THEIR APPLICATION OF ANY PRODUCTS.
THE SOFTWARE LICENSE AND LIMITED WARRANTY FOR THE ACCOMPANYING PRODUCT ARE SET FORTH IN THE INFORMATION 
PACKET THAT SHIPPED WITH THE PRODUCT AND ARE INCORPORATED HEREIN BY THIS REFERENCE. IF YOU ARE UNABLE TO 
LOCATE THE SOFTWARE LICENSE OR LIMITED WARRANTY, CONTACT YOUR CISCO REPRESENTATIVE FOR A COPY.
The Cisco implementation of TCP header compression is an adaptation of a program developed by the University of California, Berkeley (UCB) as 
part of UCB’s public domain version of the UNIX operating system. All rights reserved. Copyright © 1981, Regents of the University of California. 
NOTWITHSTANDING ANY OTHER WARRANTY HEREIN, ALL DOCUMENT FILES AND SOFTWARE OF THESE SUPPLIERS ARE 
PROVIDED “AS IS” WITH ALL FAULTS. CISCO AND THE ABOVE-NAMED SUPPLIERS DISCLAIM ALL WARRANTIES, EXPRESSED 
ORIMPLIED, INCLUDING, WITHOUT LIMITATION, THOSE OF MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND 
NONINFRINGEMENT OR ARISING FROM A COURSE OF DEALING, USAGE, OR TRADE PRACTICE.
IN NO EVENT SHALL CISCO OR ITS SUPPLIERS BE LIABLE FOR ANY INDIRECT, SPECIAL, CONSEQUENTIAL, OR INCIDENTAL 
DAMAGES, INCLUDING, WITHOUT LIMITATION, LOST PROFITS OR LOSS OR DAMAGE TO DATA ARISING OUT OF THE USE OR 
INABILITY TO USE THIS MANUAL, EVEN IF CISCO OR ITS SUPPLIERS HAVE BEEN ADVISED OF THE POSSIBILITY OF SUCH 
DAMAGES.
CCDE, CCENT, CCSI, Cisco Eos, CiscoHealthPresence, CiscoIronPort, the Ciscologo, Cisco Nurse Connect, Cisco Pulse, CiscoSensorBase, 
Cisco StackPower, Cisco StadiumVision, Cisco TelePresence, Cisco Unified Computing System, CiscoWebEx, DCE, Flip Channels, Flip for Good, 
Flip Mino, Flipshare (Design), Flip Ultra, Flip Video, Flip Video (Design), Instant Broadband, and Welcome to the Human Network are trademarks; 
Changing the Way We Work, Live, Play, and Learn, CiscoCapital, CiscoCapital (Design), Cisco:Financed (Stylized), Cisco Store, Flip Gift Card, 
and One Million Acts of Green are service marks; and Access Registrar, Aironet, AllTouch, AsyncOS, Bringing the Meeting To You, Catalyst, CCDA, 
CCDP, CCIE, CCIP, CCNA, CCNP, CCSP, CCVP, Cisco, the CiscoCertified Internetwork Expert logo, CiscoIOS, Cisco Lumin, CiscoNexus, 
Cisco Press, Cisco Systems, CiscoSystems Capital, the Cisco Systems logo, CiscoUnity, Collaboration Without Limitation, Continuum, EtherFast, 
EtherSwitch, Event Center, Explorer, Follow Me Browsing, GainMaker, iLYNX, IOS, iPhone, IronPort, the IronPort logo, Laser Link, LightStream, 
Linksys, MeetingPlace, MeetingPlace Chime Sound, MGX, Networkers, Networking Academy, PCNow, PIX, PowerKEY, PowerPanels, PowerTV, 
PowerTV (Design), PowerVu, Prisma, ProConnect, ROSA, SenderBase, SMARTnet, Spectrum Expert, StackWise, WebEx, and the WebEx logo are 
registered trademarks of Cisco Systems, Inc. and/or its affiliates in the United States and certain other countries. 
All other trademarks mentioned in this document or website are the property of their respective owners. The use of the word partner does not imply 
a partnership relationship between Cisco and any other company. (0910R)
Any Internet Protocol (IP) addresses and phone numbers used in this document are not intended to be actual addresses and phone numbers. Any 
examples, command display output, network topology diagrams, and other figures included in the document are shown for illustrative purposes only. 
Any use of actual IP addresses or phone numbers in illustrative content is unintentional and coincidental.
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
© 2011 Cisco Systems, Inc. All rights reserved.
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iii
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
CONTENTS
iii
CHAPTER
1
Getting Started with the Cisco IronPort Email Security Appliance
1-1
What’s New in This Release
1-1
Email Security Appliance Update
1-2
New Feature: Cloud User Roles
1-2
Changes to Cloud User Account Password Settings
1-3
New Feature: Outbreak Filters
1-3
New Feature: Delegated Administration
1-4
New Feature: Restrictive User Accounts and Password Settings
1-4
New Feature: Technician User Role
1-4
Enhancement: Administrator Role
1-5
Enhancement: Large Message Scanning
1-5
New Feature: SMTP Call Ahead
1-5
Enhancement: DLP Headers Scanning
1-6
New Feature: Configuration History Logs
1-6
New Feature: Scheduled Log Rollover
1-6
New Feature: Manually Download Logs Using HTTP/HTTPS
1-6
Enhancement: Service Updates Enhancements
1-7
Enhancement: IP-Based Access Through a Proxy
1-7
Enhancement: HTML Disclaimers
1-7
Enhancement: Web UI Session Timeout
1-7
Enhancement: Attachment Search Using Message Tracking
1-8
Enhancement: Reporting Enhancements
1-8
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Contents
iv
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
Enhancement: Internationalization of PDF Reports
1-8
New and Updated CLI Commands
1-8
The Email Security Appliance Documentation Set
1-9
How to Use This Guide
1-10
Before You Begin
1-11
How This Book Is Organized
1-12
Topics Discussed in the Cisco IronPort AsyncOS for Email Advanced 
Configuration Guide
1-14
The following topics are discussed in the Cisco IronPort AsyncOS for Email 
Daily Management Guide
1-15
Typographic Conventions
1-17
Where to Find More Information
1-17
Third Party Contributors
1-20
Cisco IronPort Welcomes Your Comments
1-20
Cisco IronPort Email Security Appliance Overview
1-21
Mail Flow and the Cisco IronPort M-Series Appliance
1-23
CHAPTER
2
Overview
2-1
Web-based Graphical User Interface (GUI)
2-1
Viewing Active Sessions
2-7
Command Line Interface (CLI)
2-8
Command Line Interface Conventions
2-8
General Purpose CLI Commands
2-13
CHAPTER
3
Setup and Installation
3-1
Installation Planning
3-2
Before You Begin
3-2
Installation Scenarios
3-4
Support Languages
3-7
Physical Dimensions
3-8
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v
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
Contents
Physically Connecting the Cisco IronPort Appliance 
to the Network
3-9
Configuration Scenarios
3-9
Preparing for Setup
3-12
Determine Method for Connecting to the Appliance
3-13
Determining Network and IP Address Assignments
3-15
Gathering the Setup Information
3-16
Using the System Setup Wizard
3-19
Accessing the Web-Based Graphical User Interface (GUI)
3-20
Running the Web-Based System Setup Wizard
3-20
Configuring Active Directory
3-34
Proceeding to the Next Steps
3-36
Accessing the Command Line Interface (CLI)
3-37
Running the Command Line Interface (CLI) System Setup Wizard
3-37
What’s Next: Understanding the Email Pipeline
3-56
CHAPTER
4
Understanding the Email Pipeline
4-1
Overview: Email Pipeline
4-1
Incoming / Receiving
4-5
Host Access Table (HAT), Sender Groups, and Mail Flow Policies
4-5
Received: Header
4-6
Default Domain
4-6
Bounce Verification
4-7
Domain Map
4-7
Recipient Access Table (RAT)
4-7
Alias Tables
4-7
LDAP Recipient Acceptance
4-8
SMTP Call-Ahead Recipient Validation
4-8
Work Queue / Routing
4-9
Email Pipeline and Security Services
4-9
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Contents
vi
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
LDAP Recipient Acceptance
4-10
Masquerading or LDAP Masquerading
4-10
LDAP Routing
4-11
Message Filters
4-11
Email Security Manager (Per-Recipient Scanning)
4-11
Quarantines
4-13
Delivery
4-14
Virtual gateways
4-14
Delivery Limits
4-14
Domain-Based Limits
4-14
Domain-Based Routing
4-15
Global Unsubscribe
4-15
Bounce Limits
4-15
CHAPTER
5
Configuring the Gateway to Receive Email
5-1
Receiving Email with Listeners
5-2
Enterprise Gateway Configuration
5-3
The Host Access Table (HAT): 
Sender Groups and Mail Flow Policies
5-9
Mail Flow Policies: Access Rules and Parameters
5-11
Sender Groups
5-25
Managing Sender Groups and Mail Flow Policies via the GUI
5-41
Modifying the HAT for a Listener via the GUI
5-52
Working with the HAT
5-54
Sender Verification
5-55
Sender Verification: Host
5-56
Sender Verification: Envelope Sender
5-57
Implementing Sender Verification — Example Settings
5-60
Testing Sender Verification Settings
5-68
Sender Verification and Logging
5-70
vii
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
Contents
Enabling Host DNS Verification via the CLI
5-71
Accepting Email for Local Domains or Specific Users on Public Listeners 
(RAT)
5-71
Recipient Access Table (RAT)
5-72
Modifying the RAT for a Listener via the GUI
5-76
Adding New RAT Entries
5-77
Deleting RAT Entries
5-78
Modifying RAT Entries
5-78
Changing the Order of RAT Entries
5-78
Exporting RAT Entries
5-79
Importing RAT Entries
5-79
CHAPTER
6
Email Security Manager
6-1
Overview of User-Based Policies
6-2
Incoming vs. Outgoing Messages
6-3
Policy Matching
6-4
Message Splintering
6-6
Contents of Policies
6-8
Content Filters Overview
6-9
Practical Example (GUI)
6-30
Accessing Email Security Manager
6-31
Editing the Default Policy: Anti-Spam Settings
6-33
Creating a New Policy
6-35
Creating Custom Policies
6-39
Finding Users in Policies of the Email Security Manager
6-45
Creating New Content Filters
6-47
Enabling and Applying Content Filters to Individual Policies
6-51
Notes on Configuring Content Filters in the GUI
6-54
Contents
viii
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
CHAPTER
7
Reputation Filtering
7-1
Reputation Filtering
7-2
Reputation Filtering: the Cisco IronPort SenderBase Reputation Service
7-3
SenderBase Reputation Score (SBRS)
7-4
Implementing SenderBase Reputation Filters
7-6
Configuring Reputation Filtering
7-7
Implementing Reputation Filtering in a Listener’s HAT
7-9
Testing Reputation Filtering Using the SBRS
7-11
Monitoring the Status of the SenderBase Reputation Service
7-13
CHAPTER
8
Anti-Spam
8-1
Anti-Spam Overview
8-2
Enabling Anti-Spam Scanning
8-2
Anti-Spam Scanning Engine Settings
8-4
Anti-Spam Scanning and Messages Generated by the Cisco IronPort 
Appliance
8-5
IronPort Anti-Spam Filtering
8-5
IronPort Anti-Spam and CASE: an Overview
8-6
Enabling IronPort Anti-Spam and Configuring Global Settings
8-9
IronPort Intelligent Multi-Scan Filtering
8-14
Enabling IronPort Intelligent Multi-Scan and Configuring Global 
Settings
8-15
Configuring Anti-Spam Rule Updating
8-17
Configuring Per-Recipient Policies for Anti-Spam
8-19
Positive and Suspect Spam Threshold
8-24
Positively Identified versus Suspected Spam
8-25
Unwanted Marketing Message Detection
8-25
Headers Added by IronPort Anti-Spam and Intelligent Multi-Scan
8-26
Reporting Incorrectly Classified Messages to Cisco IronPort Systems
8-27
ix
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
Contents
Testing IronPort Anti-Spam
8-27
Incoming Relays
8-30
The Incoming Relays Feature: Overview
8-31
Message Headers and Incoming Relays
8-33
Configuring the Incoming Relays Feature (GUI)
8-38
Incoming Relays and Logging
8-41
CHAPTER
9
Anti-Virus
9-1
Anti-Virus Scanning
9-2
Evaluation Key
9-2
Multi-Layer Anti-Virus Scanning
9-2
Sophos Anti-Virus Filtering
9-3
Virus Detection Engine
9-3
Virus Scanning
9-4
Detection Methods
9-4
Virus Descriptions
9-5
Sophos Alerts
9-6
When a Virus is Found
9-6
McAfee Anti-Virus Filtering
9-6
Pattern-Matching Virus Signatures
9-7
Encrypted Polymorphic Virus Detection
9-7
Heuristics Analysis
9-7
When a Virus is Found
9-8
Enabling Virus Scanning and Configuring Global Settings
9-8
Overview
9-8
Enabling Anti-Virus Scanning and Configure Global Settings
9-9
Retrieving Anti-Virus Updates via HTTP
9-10
Monitoring and Manually Checking for Updates
9-10
Configuring Virus Scanning Actions for Users
9-11
Contents
x
Cisco IronPort AsyncOS 7.5 for Email Configuration Guide
OL-25136-01
Message Scanning Settings
9-12
Message Handling Settings
9-13
Configuring Settings for Message Handling Actions
9-14
Editing the Anti-Virus Settings for a Mail Policy
9-20
Notes on Anti-Virus Configurations
9-23
Flow Diagram for Anti-Virus Actions
9-25
Testing Virus Scanning
9-27
CHAPTER
10
Outbreak Filters
10-1
Outbreak Filters Overview
10-2
Threat Categories
10-3
Outbreak Filters - Multi-Layered Targeted Protection
10-4
Cisco Security Intelligence Operations
10-5
Context Adaptive Scanning Engine
10-6
Delaying Messages
10-6
Redirecting URLs
10-7
Modifying Messages
10-8
Types of Rules: Adaptive and Outbreak
10-9
Outbreaks
10-10
Threat Levels
10-11
How the Outbreak Filters Feature Works
10-12
Dynamic Quarantine
10-14
Managing Outbreak Filters (GUI)
10-16
Configuring Outbreak Filters Global Settings
10-18
Outbreak Filters Rules
10-19
The Outbreak Filters Feature and Mail Policies
10-20
The Outbreak Filters Feature and the Outbreak Quarantine
10-26
Monitoring Outbreak Filters
10-30
Outbreak Filters Report
10-30
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