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Outbound ServicesConfiguration Guide Google Message Security Google Message Discovery Postini Email Security, Enterprise Edition

Google, Inc. 1600 Amphitheatre Parkway Mountain View, CA 94043 www.google.com

Part number: OBCG_617_13May 3, 2010 Copyright 2009 Google, Inc. All rights reserved.Google, the Google logo, Google Message Filtering, Google Message Security, Google Message Discovery, Postini, the Postini logo, Postini Perimeter Manager, Postini Threat Identification Network (PTIN), Postini Industry Heuristics, and PREEMPT are trademarks, registered trademarks, or service marks of Google, Inc. All other trademarks are the property of their respective owners. Use of any Google solution is governed by the license agreement included in your original contract. Any intellectual property rights relating to the Google services are and shall remain the exclusive property of Google, Inc. and/or its subsidiaries (Google). You may not attempt to decipher, decompile, or develop source code for any Google product or service offering, or knowingly allow others to do so. Google documentation may not be sold, resold, licensed or sublicensed and may not be transferred without the prior written consent of Google. Your right to copy this manual is limited by copyright law. Making copies, adaptations, or compilation works, without prior written authorization of Google. is prohibited by law and constitutes a punishable violation of the law. No part of this manual may be reproduced in whole or in part without the express written consent of Google. Copyright by Google, Inc. Postini, Inc. provides this publication as is without warranty of any either express or implied, including but not limited to the implied warranties of merchantability or fitness for a particular purpose. Postini, Inc. may revise this publication from time to time without notice. Some jurisdictions do not allow disclaimer of express or implied warranties in certain transactions; therefore, this statement may not apply to you. GD Graphics Copyright Notice: Google uses GD graphics. Portions copyright 1994, 1995, 1996, 1997, 1998, 1999, 2000 by Cold Spring Harbor Laboratory. Funded under Grant P41RR02188 by the National Institutes of Health. Portions copyright 1996, 1997, 1998, 1999, 2000 by Boutell.Com, Inc. Portions relating to GD2 format copyright 1999, 2000 Philip Warner. Portions relating to PNG copyright 1999, 2000 Greg Roelofs. Portions relating to libttf copyright 1999, 2000 John Ellson (ellson@lucent.com). Portions relating to JPEG copyright 2000, Doug Becker and copyright (C) 1994-1998, Thomas G. Lane. This software is based in part on the work of the Independent JPEG Group. Portions relating to WBMP copyright 2000 Maurice Szmurlo and Johan Van den Brande. Permission has been granted to copy, distribute and modify gd in any context without fee, including a commercial application, provided that this notice is present in user-accessible supporting documentation. This does not affect your ownership of the derived work itself, and the intent is to assure proper credit for the authors of gd, not to interfere with your productive use of gd. If you have questions, ask. Derived works includes all programs that utilize the library. Credit must be given in user-accessible documentation. This software is provided AS IS. The copyright holders disclaim all warranties, either express or implied, including but not limited to implied warranties of merchantability and fitness for a particular purpose, with respect to this code and accompanying

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Outbound Services Configuration Guide

documentation. Although their code does not appear in gd 1.8.4, the authors wish to thank David Koblas, David Rowley, and Hutchison Avenue Software Corporation for their prior contributions. Google Compliance Policies Notice: Google assumes no responsibility in connection with the Compliance Policies lexicon-filtering feature, including any failure to recognize credit card or social security numbers that do not follow an applicable pattern as established in Postinis systems or any failure to encrypt a credit card or social security number.

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Outbound Services Configuration Guide

Contents

What This Guide Contains 9 Related Documentation 9 How to Send Comments About This Guide

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Chapter 1: Introduction to Outbound Configuration 11 About Outbound Configuration 11 How to Use This Guide 12 Prerequisites 13 Identify Your System 13 IP Ranges 13 Set Up Reinjection 14 Register Your IP in the Administration Console 15 Increase Server Timeouts 16 Option 1: Set Up Private Outbound DNS 16 Option 2: Set Up Smarthost 19 Test Outbound Mail 19 Microsoft Exchange Servers 19 Optional: Configure SPF Records for Outbound Services 20 Alternate Option: Routing Outbound Mail on Your Firewall 21 Chapter 2: Microsoft Exchange 2003 (Private DNS Method) About Microsoft Exchange 2003 (Private DNS Method) 23 Set Up Reinjection 24 Register Your IP in the Administration Console 25 Set Up Private Outbound DNS 25 Test Outbound Mail 28 Troubleshooting 29 23

Chapter 3: Microsoft Exchange 2007/2010 (Private DNS Method) About Microsoft Exchange 2007/2010 (Private DNS Method) 31 Set Up Reinjection 32 Register Your IP in the Administration Console 40 Set Up Private Outbound DNS 40 Test Outbound Mail 43 Troubleshooting 44

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Chapter 4: Microsoft Exchange 2000/2003 Single Server (Smarthost method) 47 About Microsoft Exchange 2000/2003 Single-Server 47 Set Up Reinjection 48 Register Your IP in the Administration Console 49 Increase Server Timeouts 49 Set Up Smarthost 50 Test Outbound Mail 52 Troubleshooting 53 Chapter 5: Microsoft Exchange 2000/2003 Multi-Server (Smarthost method) 55 About Microsoft Exchange 2000/2003 Multi-Server 55 Choose Smarthost Method 56 Set Up Reinjection 57 Register Your IP in the Administration Console 58 Increase Server Timeouts 58 Set Up Smarthost 59 Test Outbound Mail 62 Troubleshooting 62 Chapter 6: Microsoft Exchange 2007 without an Edge Server (Smarthost method) 65 About Microsoft Exchange 2007 without an Edge Server 65 Set Up Reinjection 66 Register Your IP in the Administration Console 75 Set Up Smarthost 75 Test Outbound Mail 81 Troubleshooting 82 Chapter 7: Microsoft Exchange 2007 with an Edge Server (Smarthost method) 83 About Microsoft Exchange 2007 with an Edge Server 83 Set Up Reinjection 84 Register Your IP in the Administration Console 93 Set Up Smarthost 93 Test Outbound Mail 96 Troubleshooting 97 Chapter 8: Microsoft Exchange 5.5 99 About Microsoft Exchange 5.5 99 Set Up Reinjection 100 Register Your IP in the Administration Console Set Up Smarthost 100 Test Outbound Mail 101

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Chapter 9: Microsoft Small Business Server 2003 About Microsoft Small Business Server 2003 103 Set Up Reinjection 104 Register Your IP in the Administration Console 104

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Outbound Services Configuration Guide

Set Up Smarthost 104 Test Outbound Mail 105 Chapter 10: IBM Lotus Domino (Private DNS Method) About IBM Lotus Domino (Private DNS Method) 107 Choose a Private DNS Routing Method 108 Set Up Reinjection 108 Register Your IP in the Administration Console 109 Set Up Private DNS (notes.ini file) 109 Set Up Private DNS (OS Settings) 110 Test Outbound Mail 111 Troubleshooting 112 Chapter 11: IBM Lotus Domino (Smarthost Method) About IBM Lotus Domino (Smarthost Method) 115 Set Up Reinjection 116 Register Your IP in the Administration Console 116 Set Up Smarthost 117 Test Outbound Mail 117 Chapter 12: Novell Groupwise 119 About Novell Groupwise 119 Set Up Reinjection 120 Register Your IP in the Administration Console Increase Server Timeouts 120 Set Up Smarthost 121 Test Outbound Mail 121 Troubleshooting 122 Chapter 13: Sendmail 125 About Sendmail 125 Set Up Reinjection 126 Register Your IP in the Administration Console Increase Server Timeouts 127 Set Up Smarthost 127 Test Outbound Mail 127 Chapter 14: Apple Macintosh OS X 129 About Apple Macintosh OS X 129 Set Up Reinjection 130 Register Your IP in the Administration Console Set Up Smarthost 130 Test Outbound Mail 131 Chapter 15: Qmail 133 About Qmail 133 Set Up Reinjection 134 Register Your IP in the Administration Console Increase Server Timeouts 135 Set Up Smarthost 135 107

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Test Outbound Mail

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Chapter 16: Postfix 137 About Postfix 137 Set Up Reinjection 138 Register Your IP in the Administration Console Set Up Smarthost 138 Test Outbound Mail 139

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Outbound Services Configuration Guide

About This Guide

What This Guide ContainsThe Outbound Services Configuration Guide provides information about: General principles for setting up your mail server to route mail through Outbound Services. Specific steps-by-step instructions to enable reinjection and smarthosts (or Private DNS) for the most common and popular mail servers. Troubleshooting steps for the most common and popular mail servers.

This guide is intended for mail server administrators who are already familiar with mail server configuration and security. This guide is a supplement to the Message Security Administration Guide. For details about using the features and components of the email security service, see the Message Security Administration Guide. These documents are available on the Postini Support Portal. For details, see How to Send Comments About This Guide on page 10.

Related DocumentationFor additional information about Outbound Services and the email security service, refer to the following related documents. For details on how to send comments, see How to Send Comments About This Guide on page 10.Document Description

Message Security Administration Guide

See the Outbound chapter for information about