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1 IMail Server User s Guide Software Version 8.14 Ipswitch, Inc

2 Ipswitch, Inc. Web: 10 Maguire Road Phone: Suite220 Fax: Lexington, MA Copyrights Ipswitch, Inc. All rights reserved. IMail Server 8.1 User s Guide This manual, as well as the software described in it, is furnished under license and may be used or copied only in accordance with the terms of such license. Except as permitted by such license, no part of this publication may be reproduced, photocopied, stored on a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, recording, or otherwise, without the expressed prior written consent of Ipswitch, Inc. The content of this manual is furnished for informational use only, is subject to change without notice, and should not be construed as a commitment by Ipswitch, Inc. While every effort has been made to assure the accuracy of the information contained herein, Ipswitch, Inc. assumes no responsibility for errors or omissions. Ipswitch, Inc. also assumes no liability for damages resulting from the use of the information contained in this document. IMail, the IMail logo, WhatsUp, the WhatsUp logo, WS_FTP, the WS_FTP logos, Ipswitch Instant Messenger (IM), the Ipswitch Instant Messenger (IM) logo, Ipswitch, and the Ipswitch logo are trademarks of Ipswitch, Inc. Other products and their brands or company names, are or may be trademarks or registered trademarks, and are the property of their respective companies. Update History March 1995 First Edition March 1996 Second Edition August 1996 Third Edition June 1997 Fourth Edition January 1999 Fifth Edition December 1999 Sixth Edition January 2000 Seventh Edition June 2001 Eighth Edition February 2003 Ninth Edition March 2004 Tenth Edition November 2004 Online Updates v8.14

3 CONTENTS Contents Related Ipswitch Products... 1 Additional Information Sources... 2 Visit Our Web Site... 3 Technical Support... 3 Send Us Your Comments... 3 Downloading Patches and Upgrades... 4 Chapter 1 Chapter 2 Introduction New in Version Services... 6 User Interface... 6 Anti-Spam Functionality... 6 Web Messaging... 7 Basic Mail Delivery Services... 7 Additional Services... 8 Features... 9 IMail Client for Windows Directory Structure Configuration Types of Configurations Basic Configuration Advanced Configuration Viewing the Basic Configuration Root User ID A Look at Services Verifying Services Default Service Ports Checking Configuration of the Primary Host Checking the DNS Configuration for the Primary Host Setting Up DNS for the Primary Host Setting Up DNS for Multiple Mail Hosts Setting Up an Alias for a Host Adding an Additional Host Virtual Hosts with IP Addresses Virtual Hosts without IP Addresses Configuring a Virtual Host iii

4 CONTENTS Additional Host Settings Adding Hosts Based on External Databases Configuring the Primary Host Creating a Host Based on an External Database Configuring an External User Database Changing the IP Address of a Host Setting up a Dial-up Internet Connection Receiving Mail from an Internet Service Provider Setting Up the Server for Dial-up Access Setting Up a Mail Gateway Setting Up IMail Server as a Backup Mail Spooler Setting Up Peering How Peering Works Setup Procedure Example of Setting Up Peer Servers Using ETRN to Retrieve Mail Chapter 3 User Mail Accounts Working with User Accounts Adding User Mail Accounts Importing NT Users Deleting a User Mail Account Finding Orphan Mail Accounts Setting Defaults for New Users Working with Mailboxes (Directory tab) Combining Mailbox Names with User IDs Setting Up a Finger Plan Setting Up a Vacation Message Viewing the List of Sender Addresses Clearing the List of Sender Addresses Sending an Automated Response to Every Forwarding Mail to Another User Account Applying User Settings to other Users Global Settings for Existing Users Disabling All Users on a Host Creating Aliases Types of Aliases Adding an Alias Processing Mail to Users that Don t Exist iv

5 CONTENTS Chapter 4 Chapter 5 Chapter 6 Mail Processing Techniques Processing Order Setting Up Delivery Rules Rules Processing Creating an Inbound Delivery Rule Creating an Outbound Delivery Rule for a Host Adding Multiple Conditions to Rules Processing Order for Conditions Order of Rules Testing a Delivery Rule Rule Syntax Determining Which Rule Trapped a Message Storing Search Text in External Files Limitations Commonly Used Rule Examples Note to Killer WebMail and Classic WebMail Users Using the Info Manager Using the Info Manager for a Single Automated Response When to Use a Sub-divided Info Manager Account Sub-areas and Mailboxes Sub-dividing an Info Manager Account Notes about Forwarding Disabling the Info Manager More About the Info Manager SMTP Server SMTP RFCs Supported Basic Information Logging On Configuring the SMTP Server SMTP Options Using a Remote Mail Gateway SMTP Security Advanced Options SMTP Security Background on SMTP Protocol Security Security Strategies Mail Relay Validating Incoming Mail Access Control Options v

6 CONTENTS Changing the SMTP Hello Message Setting SMTP Security Options Setting Mail Relay Options Mail Relay Options Setting Access to Local Mail Groups Validating Incoming Mail Setting Access to the SMTP Server Copying Inbound and Outbound Mail Chapter 7 Chapter 8 Chapter 9 POP3 Server Logging On Configuring the POP3 Server Logging Options Other Options Advanced Options Change the POP3 Hello Message: Setting Access to the POP3 Server IMAP4 Server IMAP4 Implementation IMAP4 Server Support Full IMAP4 Client Support Mailbox Management Public Mailboxes Logging On Configuring the IMAP4 Server Logging Options Conditional Options Advanced Options Changing the IMAP 4 Hello Message: IMail Web Messaging What is Web Messaging? What Can Users Do with Web Messaging? System Requirements Web Messaging Security Using Secure Sockets Layer (SSL) Troubleshooting SSL Setting Up Web Messaging Web Address for the Web Messaging Server Multiple Mail Hosts vi

7 CONTENTS Configuring the Web Server Advanced Tab Setting Access to Web Messaging Features Using Remote Administration Features User Administration Alias Administration List Administration Viewing Monitor Logs and the Spool Directory Managing Virtual Hosts Managing Mailing Lists Creating Delivery Rules Editing the News of the Day and Welcome Messages Spell Checker Installing Dictionaries For Hosts Enabling Spell Check Accessing Spell Check Disabling Spell Check Editing Dictionaries Dictionary Explanations Displaying Online Advertisements Editing the Welcome Message Editing the News of the Day Multi-Lingual Support Customizing Web Messaging Chapter 10 IMail Web Calendaring What is IMail Web Calendaring? What Can Users Do? System Requirements Security Using Secure Sockets Layer (SSL) Starting an SSL Connection from a Browser The Web Address for IMail Web Calendaring If You Have Multiple Mail Hosts Configuring the Web Calendaring Server Setting Access to IMail Web Calendaring Features Invitations Sending Invitations Viewing Invitations Accepting Invitations Declining Invitations Displaying Online Advertisements Customizing IMail Web Calendaring vii

8 CONTENTS Chapter 11 Chapter 12 Chapter 13 Chapter 14 The Monitor Server Configuring the Monitor Server Logging On Changing Monitor Settings in the Control Panel Working with Notifications Defining a Notification Defining Beeper Notifications Using an External Beeper Program Defining Pager Notifications Defining Notifications Adding Notifications to the Notifications Tab Enabling Notifications Disabling Notifications Web Administration Feature Configuring Web Administration Setting Access to Web Administration Using the Web Administration Capability Personal Account Options System Administration Host Administration LDAP Server LDAP Implementation Full LDAP Directory Support LDAP Directory Structure Supplying LDAP Information for Unregistered Users Accessing LDAP Information from Microsoft Mail Clients 165 Populating the LDAP Database Logging On Configuring Options Enabling LDAP Administrators (Host s LDAP tab) Password Server Configuring the Password Server Logging Options Logging On Whois Server Logging On Configuring the Whois Server viii

9 CONTENTS Options Logging Options Chapter 15 Chapter 16 Chapter 17 Finger Server Logging On Configuring the Finger Server Logging Options Queue Manager Configuring the Queue Manager Options DNS Cache Options Failed Domain Skipping Options The Mail Queue Viewing Files in the Queue Files in the Queue Beginning Character in File Name File Extensions Attachments List-Server Mailing Lists Features How the List Server Works Types of Mailing Lists Open Lists (Anyone Can Post) Subscriber Lists Moderated Lists Using Passwords and Posters Lists Posting to a List Using a Password Requesting Information and Subscribing Format of Requests Commands for Requesting Information Commands for Subscribing and Unsubscribing Commands for the Use of Subscribers Commands for the Use of the List Owner (or Moderator) Creating a Mailing List Setting Advanced Options Setting List-Server Security Setting Up Digest Mode Set up digest mode for a list-server mailing list ix

10 CONTENTS Digest Scheduling Removing Subscribers and Unknown Users Setting Up an Alias to Remove an Unknown User Setting Up an Alias to Automatically Delete a User Chapter 18 Anti-Spam Features Overview Anti-Spam Features Accessing Anti-Spam Features Overview of Setup Tasks Server Configuration Host Configuration Processing Order Server Configuration Configuring DNS Black Lists Configuring a DNS Black List for the Server Options Enabling/Disabling DNS Black lists Enabling Logging Host Configuration Connection Filtering Enabling/Disabling DNS Black lists Changing a Black List Type Validation Tests Display Labels Content Filtering Statistical Filtering Options Setting Up the Exclude List Phrase Filtering Setting Up the Phrase List Editing the Phrase List Options Merging Multiple Phrase Lists What to Enter in the Phrase List HTML Content Filtering HTML Feature Filtering Options URL Domain Black List Options Adding a Domain to the URL Domain Black List Editing a Domain in the URL Domain Black List Merging Multiple URL Domain Black Lists x

11 CONTENTS Configuring Trusted Addresses Adding Trusted Addresses Display Options Advanced Configuration Advanced Statistical Filtering Options Using Delivery Rules to Filter Spam Bouncing Spam Messages Forward Spam messages to a Specific User Folder X-Header Explanations Updating the antispam-table.txt File Command Syntax Reading the Antispam-table.txt File Modifying the antispam-table.txt File Resolving Incorrectly Identified Resolving False Positives in the Antispam-table.txt File Using one Antispam-table.txt File for All Hosts Creating Separate Antispam-table.txt Files for Hosts Customizing the Antispam-table.txt File Entering New Words into the Antispam-table.txt File Changing word counts for individual words Deleting Words from the Antispam-table.txt File Merging antispam-table.txt Files Creating a URL Domain Black List From a Mailbox Creating a URL Domain Black List and antispam-table.txt 244 Configuring the Anti-Spam Engine to Identify Wildcards Preparing Mailboxes for use with antispamseeder.exe Logging Logging Tab File Format Log Message Components Anti-Spam Administration in Web Messaging Accessing the Anti-Spam Web Messaging Pages Navigating the Anti-Spam Pages Frequently Asked Questions Troubleshooting Chapter 19 Remote Administration Requirements for Connection Password Server Setup Connecting to a Remote Server xi

12 CONTENTS Chapter 20 Chapter 21 Sending Mail to a Pager or Beeper Adding a Beeper or Pager Alias Defining a Pager Alias Defining a Beeper Alias Sending a Message to a Pager/Beeper Forwarding a Message to a Pager Sending a Message to a Beeper When Mail Arrives Command Line Applications Adding Aliases (addalias.exe) Basic Command Syntax Adding an Alias to the Primary Host Adding an Alias to a Specific Host Deleting an Alias Importing a Windows NT Group as a Group Alias Return Codes Using a Text File Adding Virtual Hosts (adddomain.exe) Basic Command Syntax and Example Adding Users (adduser.exe) Basic Command Syntax Adding a User ID Deleting a User ID Return Codes Using a Text File Disabling Web Options Sample File Sending Mail (imail1.exe) Command Syntax Deleting Old Messages (immsgexp.exe) Basic Command Syntax Example Populating the LDAP Database (ldaper.exe) Basic Command Syntax Sending Mail to All Users (mailall.exe) Basic Command Syntax Examples Backing Up IMail Server Configuration (regback.exe) Basic Syntax Command Delivering Mail (smtp32.exe) Processing Rules for smtp32 (and imail1) Cleaning the Spool Directory (isplcln.exe) xii

13 CONTENTS Basic Command Syntax Example Merging\Cleaning Phrase Lists and URL Domain Black Lists (cleanlist.exe) Basic Command Syntax Merging Phrase lists Merging URL Domain Black Lists Deleting Duplicate Entries in the URL Domain Black List. 276 Example Example Deleting Duplicate Entries from the Phrase List A B C Backups Backing Up the IMail Server Configuration Using IMail Administrator to Back Up the Registry Using a Command Line Utility Using Regedit Backing Up IMail Server System Files Backing Up User Mail Log Files Mail Server Log Files Typical Log Files Large Log Files Disabling Logging Troubleshooting File Locking IMail Log Analyzer Analyzing a Log File Search Options Report Types Interpreting the Analysis Running Log Analyzer as a Command Line Utility Basic Command Syntax Example Command Line Entry Anti-Spam Log Messages Connection Filtering Content Filtering xiii

14 CONTENTS D E F G Default Registry Values Special Registry Values Deleting an IP Address Not in Use Customizing Text for Bounce Messages Changing the number of Times Black Lists Retry a DNS Query Refuse Null Senders Customizing Templates Web Files and Directory Structure Directory Structure for Multiple Hosts Editing Web Templates Web Templates and their Associated Web Pages Customizing a Web Page Editing Tips Configuration Files Edit colors Changing Button Labels and Logos Edit Header and Footer Globally Editing the Language Displays Miscellaneous Customizations Creating and Editing Language Pack Files Editing Language Pack Files Creating New Language Pack Files IMail Tags Tag Syntax Web Messaging Web Calendaring Types of Tags ParseExtensions Directory Location Adding ParseExtensions to the Registry Copyrights Spell Check Dictionaries MD5- Message-Digest Algorithm SSL Implementation OpenLDAP Licenses xiv

15 CONTENTS Glossary Index xv

16 CONTENTS xvi

17 Ipswitch produces a variety of products that enhance and compliment the capacity of IMail Server. The products below are the most popular add-on products for IMail Server. For a complete list of products, visit the Ipswitch website at Related Ipswitch Products These products must be purchased separately from IMail Server. Ipswitch Instant Messenger. Provides instant messaging in a secure environment, using 3DES encryption on communications between client and server. The server can be placed behind a firewall to stop conversations from going out over the Internet. Conversation logging helps enforce usage policies, comply with communication archiving laws (such as SEC or HIPAA requirements), and record conversations. IMail Server Mail-to-Fax. Allows system administrators to create aliases that route messages directly to a fax machine. This allows ISPs to set up accounts for customers who do not have a PC or Internet access and want to receive messages via a fax machine. Other users can send faxes from their desks by sending to a special account on a local server that faxes it to the recipient. IMail Anti-Virus (Standard and Premium). IMail Anti-Virus fully integrates into the IMail Administrator interface. It is a high performance, reliable product that stops viruses before they get to a user s client. IMail Anti-Virus gives administrators a powerful all-in-one anti-virus solution that is easy to install and use. Preface In This Chapter Related Ipswitch Products Additional Information Sources Visit the Ipswitch Website Technical Support Send Us Your Comments Downloading Patches and Upgrades 1

18 PREFACE Killer WebMail Templates. These Web Messaging templates provide an easy-to-customize interface that looks and feels like a standard client. Users can choose from 23 different styles. The templates also support virtual host logins using just the username, a multi-frame layout to simultaneously view folders, a message summary and the message body all on one screen, and multiple language displays. EZSignUp. Users can create their own user accounts using a combination of Active Server Pages and IMail Server's command line utilities. This is a convenient way for administrators to provide an auto-signup for IMail Server. Killer LDAP. Killer WebMail users can search for addresses against one or more LDAP servers, including IMail Server's LDAP server, using this Killer LDAP searchable address book. This is a convenient way to provide a centrally managed, global address book to all users. You ve Got IMail. You've Got IMail integrates the Killer WebMail templates with regular web pages, providing a login form, new message count and send functions. Users can see how many new messages they have or send an via the Killer Web- Mail compose screen from a web page without logging in. Listbuilder. The Listbuilder allows for easy creation of list files for IMail Server lists. It has an easy-to-use graphical interface listing all IMail Server hosts. It can also combine several hosts into one mailing list and filter users based on their enabled status or administrative level. Externalizer. Allows for easy migration from the IMail Server database to a Microsoft Access or Microsoft SQL Server database. Additional Information Sources IMail Getting Started Guide. This printed booklet contains the installation instructions for IMail Server, as well as information to plan your installation. It also includes an introduction to DNS. This booklet is available in pdf format in the IMail top directory. Application Help. Help is always available by clicking Help or pressing F1 in all Ipswitch products. Release Notes (ntimsvc.txt). The release notes, located in the IMail top directory, provide an overview of the changes for the current release, as well as known issues and bug fixes. Also included are template additions and modifications. IMail Tag reference (Tags.doc). This document, located in the IMail top directory/web folder, lists all IMail tags used in the web messaging templates, and how to use them to customize the product. 2

19 PREFACE Web Calendaring tags Reference (iwebcaltags.doc). This document, located in the IMail top directory/web/calendar folder, lists and explains all IMail tags used in web calendaring, and how to use them to customize the product. Discussion list. The IMail Server discussion list is an opportunity to interact with other IMail Server customers to share tips and tricks for using IMail Server. You can sign up for the discussion list in the IMail Support Center at Visit Our Web Site For more information about Ipswitch products, to find evaluation versions, or purchase our products, visit the Ipswitch web site at: On our technical support pages, you can view the Knowledge Base of technical information and keep up-to-date on product news. You can also browse through our template gallery to get a different look and feel for Web Messaging., and visit the user created utilities page for a list of useful programs. Technical Support The IMail Support center provides a multitude of resources including the following: DNS Help, a Template Gallery, Discussion list signup, IMail Server Utilities, HTML versions of the manuals, and updated versions of the antispam-table.txt file, phrase list, and URL Domain Black List. It also lists tech support contact information, support hours and information about service agreements. You can access the IMail support center at the following address: Send Us Your Comments We welcome your feedback on this product and its documentation. Please send your comments and suggestions to the following address:feedback@ipswitch.com. 3

20 PREFACE Downloading Patches and Upgrades If a software patch is created to fix a bug in the currently shipping version of a product, Ipswitch places the patch on our web site. Product upgrades are also available on our FTP and web sites. A service agreement for IMail Server includes major product upgrades for twelve months. Check our web site for current software patches and upgrades. 1 In your web browser, go to: 2 Click the IMail Server link. 3 Read the introductory information about patches and upgrades at the top of the page. 4 Select the appropriate patch or upgrade. 5 Follow the instructions on your screen. 4

21 Introduction IMail Server is an electronic mail solution for Internet and intranet messaging requirements. Easy to install and administer, IMail Server significantly reduces the cost of mail implementation and administration. Its features improve productivity and provide an alternative to proprietary systems or complicated UNIX-based Internet mail. IMail Server uses Simple Mail Transfer Protocol (SMTP) to send and receive mail over the Internet or internal TCP/IP network. There are also servers for LDAP, Finger, and Whois information. The Web Administration capability of the Monitor server allows system administrators to monitor the system and perform maintenance using a web browser on any computer. They can receive a notification when a service is down, and restart it. IMail Server provides: Full integration with the Windows user database Ability to base user mail accounts on an external database IMail Server can be read with: Any POP3 mail client Any IMAP4 mail client Any web browser This Internet standards based client/server architecture provides system administrators with flexibility to set up a mail solution that easily accommodates different and/or geographically dispersed mail clients. Note: For information since this manual was printed, see the Release Notes (Ntimsvc.txt) in the IMail top directory. Chapter 1 In This Chapter New in Version 8.1 Basic Services Additional Services Features IMail Client Directory Structure 5

22 CHAPTER 1 Introduction New in Version 8.1 Enhanced the ability to track a message using a single message ID, which persists across all SMTP, Queue Manager and anti-spam logs. The IMail Log Analyzer compiles reports based on log files and separates information into 19 reports, enabling you to browse information such as: number of SMTPD connections, number of IMAP errors, number of web logins, number of web hits, and more. A Compact Mailbox Percentage option allows system administrators to specify how much wasted space a mailbox can contain before it is compacted. Services SMTP Access Control provides the ability to skip all spam checks for listed IP addresses. OpenLDAP technology provides a more robust way to manage LDAP data. Existing LDAP databases are converted into OpenLDAP databases during installation. New OpenSLL technology and a new SSL Configuration Utility provides a better way to create SSL certificates. Access Control List (ACL) functionality has been incorporated into the IMAP server. A new add-on allows integration with Microsoft Outlook. User Interface New host s LDAP tab allows you to define an LDAP administrator. Anti-Spam Functionality The anti-spam message ID is inserted into X-Headers. New spam action in content filtering, HTML content filtering and URL Domain Black List allows you to move spam messages to a mailbox. New HTML filtering option for non-primary hosts allows you to use the primary domain s HTML filtering configuration. Content Filtering now supports subject modification for spam messages. Administrators can insert customizable text into the Subject of messages identified as spam. In Phrase Filtering, added the ability to search only the Subject, only the Body, or the Subject and Body for specified phrases. New Trusted Addresses tab allows you to enter IP addresses, addresses, and domains on which no content filtering is performed. 6

23 Introduction CHAPTER 1 Web Messaging The web templates have been replaced to increase functionality and ease of customization. The new default templates are the Classic WebMail templates, which can be displayed in other languages including: Dutch, German, Japanese, Korean, French, Chinese, Spanish. Basic Mail Delivery Services SMTP (Simple Mail Transfer Protocol) POP3 (Post Office Protocol) IMAP4 (Internet Message Access Protocol version 4) Web Messaging Sends and receives mail from other servers using the SMTP Protocol. SMTP authentication methods are supported to provide a secure means of sending user IDs and passwords across networks. You control access to the SMTP server, by specifying an IP address or IP range that are either granted or denied access. Mail relay options provide additional security, by defining who can send mail through your server. For information on SMTP, see SMTP Server on page 81. POP3 mail clients can communicate with IMail Server. POP3 is the most common protocol for retrieving messages from a mail server. POP3 servers hold messages until users download them to their local machine. For information on POP3 see POP3 Server on page 99. Allows clients to access messages remotely. stored on an IMAP server can be accessed from a home computer without transferring messages between computers. Like POP3, IMAP4 uses SMTP for communication between the client and server. For information on IMAP4 see IMAP4 Server on page 105. Allows users to access mail using any web browser. Users can maintain an address book, manage mailboxes, and use delivery rules to process incoming mail. Web messaging is equipped with a Spell Checker and various dictionaries. Administrators can manage virtual hosts, aliases, users and list-server mailing lists. They can also customize the web templates to change their look and functionality. Web Messaging also supports online advertising. For information on Web Messaging see IMail Web Messaging on page

24 CHAPTER 1 Introduction Additional Services Web Calendaring A Lightweight Directory Access Protocol (LDAP) version 3 server A list server A web-based calendar accessible from any web browser. IMail Web Calendaring provides a user-friendly interface for storing schedules, setting appointments, recording notes and tasks, and receiving reminders for appointments. Users can also send requests to others inviting them to appointments or events. IMail Web Calendaring also supports online advertising. For information on Web Calendaring see IMail Web Calendaring on page 133. Allows remote access to user data through any LDAP client. User data includes standard LDAP information such as the user s name, organization, mailing address, and telephone number. For information see LDAP Server on page 163. Allows you set up automated mailing lists, which receives mail and resends it to all users on the list. The list server supports moderated and unmoderated lists, and the ability to group messages into a digest. For information see List-Server Mailing Lists on page 187. Monitor server Monitors each service by polling. It can be configured to send , beeper, or pager notifications and restart a service that is down. It can also monitor other services (DNS, NNTP, WWW, Telnet, and FTP), the default gateway, and disk space, from either the local or a remote system. You can access the Monitor server remotely using a web browser to view the status of services and perform administration functions. For more information see The Monitor Server on page 145. Finger and Whois servers These servers allow you to publish user information on the Internet. For information see Finger Server on page 177. A Password server Allows users of older mail clients (Eudora and NuPOP) to change their passwords remotely. Queue Manager service Provides control over the flow of messages through the queue by allowing you to set options based on your system s needs. The queue manager can regulate SMTP32 threads so the maximum is not exceeded. A daily report can be sent to administrators detailing the server s performance. 8

25 Introduction CHAPTER 1 Features User Registration and Maintenance Mailing List Creation and Maintenance Mail Forwarding Vacation Support Finger Plan Support Mail Delivery Rules Automated Mail Accounts (Info Manager) Multiple Host (Domain) Support User accounts can be based on an external database using the ODBC method, but can be extended to include up to ten different methods. Administrators can add, delete, and manage user accounts, create aliases, and update Whois, and LDAP information. Command line utilities can be used to add or delete users from text files, delete old messages in a user account, and send a message to all users on a host or on the entire server. For information on user accounts, see User Mail Accounts on page 39 and Command Line Applications on page 261. IMail Server can create and maintain public and private mailing lists.when a mailing list receives mail, it re-sends the mail to all subscribers. Messages can be sent one at a time, or in digest form. For information, See List-Server Mailing Lists on page 187. IMail Server can forward new mail for a user to another address. For information, See Forwarding Mail to Another User Account on page 50. If a user cannot answer mail due to vacation or other absence, IMail Server can send one notice to each person who sends mail to that user. For information, See Setting Up a Vacation Message on page 48. Allows remote users to see information about users registered on a system, including the user s full name, address, and a Plan file provided by the user containing any additional information the user wishes to provide. For information, See Finger Server on page 177. Delivery rules search for particular text patterns in the content of a particular part of a message (To, From, Sender, Subject, entire header, or message body) and re-route the message. You can apply delivery rules for a mail host, a mailing list, or users. For information, See Setting Up Delivery Rules on page 59. Allows you to set up an automated response for messages. When mail is received for a user that has enabled the Info Manager, a message is sent back to the sender. For information, See Using the Info Manager on page 75. To receive mail for more than one mail host on the same system, you can set up multiple virtual hosts. For information, See Configuration on page 13. 9

26 CHAPTER 1 Introduction Privacy-Enhanced POP Support Forwarding of Mail to a Beeper or Pager Unknown Local User Processing Anti-Spam Features Post Office Protocol Version 3 (POP3) is the most common protocol used by mail clients for retrieving messages from a mail server. The user ID and password are encoded so they cannot be read by standard text editors. For information, See POP3 Server on page 99. IMail Server can route inbound mail to an external program such as pager or beeper addresses, or any other application. For information, See Types of Aliases on page 53. IMail Server can process mail that is incorrectly-addressed or addressed to users that don t exist. This is accomplished through the nobody alias, which sends mail to a specified program or another user s mailbox. For information, See Processing Mail to Users that Don t Exist on page 56. IMail Server s built-in messaging controls prevent spammers from using IMail Server as a relay or gateway. You can set up the server to accept only mail that originates from or is destined for local users. You can also block incoming messages from IP addresses that have been a source of spam. For more information, See SMTP Security on page 87. Anti-spam features also catch spam messages by examining the message content and comparing the IP addresses against configurable black lists. For information see Anti-Spam Features on page 205. IMail Client for Windows A special version of IMail Client for Windows is installed on the IMail system. This is provided for those who administer IMail Server on the workstation on which IMail Server is installed; it is useful for reading the root mailbox, working with seldom-used accounts, and testing. Note: The IMail Client application should not be used on the IMail Server system to view end-user mailboxes, as this may cause problems with remote access to the same mailboxes (depending on the remote clients being used). Directory Structure The IMail directory, usually C:\IMail, is the top directory, which contains all IMail Server applications and the directories for the primary host. You specify this directory during installation, and should never move or change it. Each host directory contains the following: 10

27 Introduction CHAPTER 1 The Lists directory contains all mailing lists and text files that are referenced by group aliases. The Spool directory where messages are processed (the queue) and where log files are kept. For information, See Log Files on page 281. Note: Only the IMail TopDir has a spool directory. The Web directory contains templates, ads, and monitor files. The Users directory contains the users on the host. Within the Users directory, each user has a directory. Within each user s directory are the user id file (.uid); mailbox files (.mbx); index files (.idx); finger plan, vacation, rules, and forwarding files (.ima). The OpenLDAP directory contains all files related to the OpenLDAP implementation including the OpenLDAP binaries, schema files, and the openldap-data files which contain domain specific databases The cfg directory contains information for the IMail Client application. 11

28 CHAPTER 1 Introduction 12

29 Configuration This chapter describes how to configure your mail server and the Domain Name System (DNS) records pertaining to mail service. It also describes how to create multiple mail hosts and discusses the DNS records required for multiple hosts. It also covers a number of advanced configuration topics. Types of Configurations Basic Configuration If your mail server will receive mail for only one domain, read Checking Configuration of the Primary Host on page 17, Setting Up DNS for the Primary Host on page 18, and Viewing the Basic Configuration on page 14. For background information on DNS servers, see Appendix A: Mail Servers and the DNS in the IMail Server Getting Started Guide. Advanced Configuration Depending on your mail requirements, you may want to read some of the following advanced configuration topics: You can set up an alias for the official host name (entered during installation), so that IMail Server recognizes another name as valid. For example, you could set up an alias so that both user@mail.domain.com and user@domain.com are valid addresses. To set up an alias, see Setting Up an Alias for a Host on page 19. If the server will receive mail for multiple domains (example, for domain1.com and domain2.com), see Adding an Additional Host on page 20. If your mail server will function as an SMTP mail gateway for proprietary mail systems such as Microsoft Exchange or CC:Mail, see Setting Up a Mail Gateway on page 33. Chapter 2 In This Chapter Types of Configurations The Basic Configuration A Look at Services Setting Up an Alias Checking Configuration of the Primary Host Adding an Additional Host Hosts based on External Databases Changing a Host s IP Address Setting Up Dial-Up Connections Setting Up a Mail Gateway Setting Up a Backup Mail Spooler Setting Up Peering Using ETRN to Retrieve Mail 13

30 CHAPTER 2 Configuration If you have a dial-up Internet connection from your mail server to an Internet Service Provider (ISP), see Setting up a Dial-up Internet Connection on page 29. To set up IMail Server as a backup mail server for another server, see Setting Up IMail Server as a Backup Mail Spooler on page 34. To spread user accounts across two or more computers, you can set up peer servers. For example, mail sent to domain.com is processed by both host1.domain.com and host2.domain.com. See Setting Up Peering on page 35 for more information. To specify how your mail server relays mail for other servers, see SMTP Security on page 87 for information. Viewing the Basic Configuration In the left panel, select localhost to view the IMail Server configuration. The General tab shows host and directory information. You can modify only the Gate Host and the Default Host properties. The Gate Host is the name of another host to send mail to for further delivery when it cannot be delivered to the destination host. This can be used in conjunction with Send all remote mail through gateway on the SMTP tab to force delivery of mail through the gateway host. This is useful for dial-up connections. Since IMail Server should be able to reach all hosts directly, this field should typically be blank. See also SMTP Server on page

31 Configuration CHAPTER 2 The Default Host box displays the host name to which mail is delivered if the original recipient address contains only a user ID without a host name, and that user ID is not found on the sender s host. Normally, this field should be blank or set to localhost. Otherwise, mail is sent to userid@defaulthost, which may not be the intended recipient. This field can be useful when multiple systems are required to work as one. Note: Setting this option incorrectly may cause mail to be sent to unintended recipients. Root User ID Each host in IMail Server must have user ID of root and an alias of postmaster in order to comply with the SMTP RFCs. These allow messages to be sent to the server by other hosts, and allow certain system messages (such as error messages) to be automatically generated. If the primary host uses the IMail database or an external database, the installation procedure creates a user named root and an alias named postmaster and points the alias to the user named root. The user ID of root is automatically registered, however the account is disabled by default. When using the NT user database, the installation creates a user named administrator and an alias named postmaster and points the alias to the user name administrator. 15

32 CHAPTER 2 Configuration A Look at Services Click the Services folder to see the IMail services and their current status. Later chapters describe the configuration options available for each service. Click the service name to modify its properties. Status of services Verifying Services You can modify configurations for each service by expanding the Services folder in the left panel, clicking the appropriate service name underneath it, and modifying the settings in the right panel. After changing parameters, stop the service, wait five to ten seconds, then start the service. Default Service Ports ITCP ports: SMTP: Port 25 POP3: Port 110 IMAP4: Port 143 LDAP: Port 389 Pserve (Password Server): Port 106 Web Messaging: Port 8383 by default (configurable) 16

33 Configuration CHAPTER 2 Web Messaging SSL Port: 8384 Spell Checker Port: 8385 by default (configurable) Web Calendaring: Port 8484 by default (configurable) Web Calendaring SSL: Port 8485 SSL: Port 8384 by default (configurable) IMonitor Web Administration: Port 8181 by default (configurable) Web Messaging and Web Calendaring also use several UDP ports: Web Messaging: Port 8000 Web Calendaring: Port 8001 These ports, are used to facilitate communications between Web Messaging and Web Calendaring, such as receiving the user key and sending the user ID and password. Checking Configuration of the Primary Host After installing IMail Server, you have a single mail host configured (the primary mail host). Check the following items in the primary mail host configuration: This primary mail host must have the same name as the host on which you installed IMail Server. This is the official host name that you see when you expand the localhost folder in the left panel. If you do not want to use the official host name of your server as the name of the primary mail host, you can create an alias for the primary mail host. See Setting Up an Alias for a Host on page 19 for information. The domain name for the local network must be set in your Windows configuration. To check the domain name for your local network (in Windows), double-click the Network icon in the Control Panel, select the Protocols tab, then select TCP/IP Protocol in the list, and click Properties. The Microsoft TCP/IP Properties dialog box appears. Click the DNS tab to view domain information. To check the DNS information (on Windows 2000), double click the System icon in the Control Panel, select the Network Identification tab, then click Properties. The Identification Changes dialog box appears which displays the domain information. 17

34 CHAPTER 2 Configuration The DNS server for the local network must appear on the IMail Administrator SMTP tab. To check the DNS server setting, click the SMTP tab. In the Domain Name Server address box, you should see the IP address of your DNS server. Note: You can see your own DNS records (and those of any host) with the Lookup utility in Ipswitch's WS_Ping ProPack, a network information tool. An evaluation version of WS_Ping ProPack is included on the IMail Server CD, and is available on the Ipswitch website: Checking the DNS Configuration for the Primary Host For background information about DNS records, see Appendix A: Mail Servers and the DNS in the IMail Server Getting Started Guide. Setting Up DNS for the Primary Host Verify or create the following entries for your primary mail host in your DNS: An MX record for the mail domain (for example, domain.com). The MX record identifies the host name of the computer running the mail server (the IMail Server computer). An A record for the host name of the computer running IMail Server. The A record maps a host name to an IP address. A PTR record for the IP address of the computer running IMail Server. The PTR record maps an IP address to the host name and is used for reverse lookups. Example: The DNS entries for a host with an official host name of mail.domain.com would look like: SOA $ORIGIN... domain.com IN MX 10 mail.domain.com(mx record) mail IN A (A record) in-addr.arpa.,type = PTR host = mail.domain.com (PTR record) A DNS lookup for mail sent to user@domain.com would find that the mail must be sent to the host mail.domain.com. Setting Up DNS for Multiple Mail Hosts For a virtual host with an IP address, you must make the following entries in your DNS: An MX record for the mail domain (i.e. mail.domain2.com). The MX record identifies the host name of the virtual host. 18

35 Configuration CHAPTER 2 An A record for the host name of the virtual host. The A record maps a host name to an IP address. A PTR record for the IP address of the virtual host. The PTR record maps an IP address to the host name and is used for reverse lookups. Example: The DNS entries for a virtual host with a host name of mail.domain2.com would look like: SOA $ORIGIN... domain2.com IN MX 10 mail.domain2.com(mx record) mail IN A (A record) in-addr.arpa.,type = PTR host = mail.domain.com (PTR record) A DNS lookup for mail sent to user@domain2.com would find that the mail must be sent to the host mail.domain2.com. For a virtual host without an IP address, you must make only one entry in your DNS: an MX record for the mail domain (i.e. mail.domain3.com). This MX record identifies the host name of the primary mail host. As an example, the DNS entries for a virtual host without IP address for which the host name is mail.domain3.com would look like: SOA $ORIGIN... domain3.com IN MX 10 mail.domain.com A DNS lookup for mail sent to user@domain3.com would find that the mail needs to be sent to the host mail.domain.com. Setting Up an Alias for a Host IMail Server accepts mail addressed to the official host name of the system on which IMail Server is installed. You can set up an alias for the official host name so that IMail Server recognizes another name as valid. For example, if the official host name is mail.domain.com, you can receive mail addressed to user@mail.domain.com, where user is a valid user on the host. If you also want IMail Server to accept mail addressed to user@domain.com, you must enter domain.com as an alias for the official host name. 19

36 CHAPTER 2 Configuration To set up an alias for the official host name: 1 In the left panel, select the mail host. The mail host properties appear. 2 In the Aliases box, enter the alias name (i.e. domain.com). Separate multiple aliases with a space. This field is limited to 255 characters. 3 Click Apply. Adding an Additional Host If you want IMail Server to receive mail for a second domain with its own users, you must set up a virtual host for the second domain. For example, if your mail server provides mail service for domain1.com, and you also want it to provide mail service for domain2.com, you must create a virtual host for domain2.com. There are two types of virtual hosts: Virtual hosts with IP Addresses Virtual hosts without IP addresses Note: Whether you use a virtual host with an IP address or without an IP address, you must make DNS entries for your domain(s). See Setting Up DNS for Multiple Mail Hosts on page 18 and your DNS documentation for information on creating these entries. Virtual Hosts with IP Addresses This is the recommended way to set up virtual hosts, because all capabilities of regular IMail Server hosts are available to virtual hosts with IP addresses. The only limitations of virtual hosts with IP addresses are: Each virtual host requires its own unique IP address. In Windows NT/2000, this requires the extra step of adding an IP address in the Windows NT TCP/IP configuration in the Control Panel (Network applet - > Protocols -> TCP/IP Protocol -> Advanced.) Note: If you are using Windows NT or later, you can add up to five IP addresses in the Network applet. If you need to add more than five addresses, refer to the documentation for Windows NT/

37 Configuration CHAPTER 2 Virtual Hosts without IP Addresses Virtual hosts without IP addresses are easier to set up than those with IP addresses. For more information, see Configuring a Virtual Host on page 21. The IMail Server computer assigns a virtual IP address for the selected domain. You can then use an MX record in your DNS to point the virtual host to the primary host (which has a real IP address). There are several limitations of virtual hosts without IP addresses: When users log on, they must enter the entire userid@hostname.com string for their user ID, so that IMail Server can tell which virtual host the user is associated with. Some mail clients are not able to connect to the virtual host to read mail. This problem exists because some mail clients either have length restrictions for user IDs, or they clip the user ID at sign. You can configure virtual hosts to use a different character to separate the user ID from the hostname, but then you must tell users to use this character in their logon user IDs (for example, userid#hostname.com). To change the character, see Special Registry Values on page 303. The LDAP, Whois, and Finger servers do not work for virtual hosts without IP addresses. Virtual hosts without IP addresses are recommended when you have a shortage of IP addresses, or when you want to forward all mail for a domain to a user at another domain. Here is an example of the latter: Your primary domain is called abracadabra.com. You want all mail sent to merlin.com to be forwarded to info@abracadabra.com. To accomplish this: 1 Set up a virtual host without an IP address for merlin.com and do not create any users for merlin.com. 2 Set up a nobody alias for merlin.com pointing to a user ID on abracadabra.com All mail to any user at merlin.com is sent to the specified user at abracadabra.com Configuring a Virtual Host (assuming Tools > Use Wizards is cleared): 1 Select the localhost folder in the left panel. 2 Click Add Host. The Virtual Host Configuration dialog box appears. 21

38 CHAPTER 2 Configuration The Local Addresses list box shows all IP addresses set up in the Windows TCP/IP properties and any virtual IP addresses assigned by the IMail Server. 3 Select the IP address for the virtual host (in the Local Addresses list box) or click Add to assign a new virtual IP address to use for the new mail domain. 4 For the Official Host Name, enter the name of the mail host. The name entered is used to address mail to the users on the virtual host. For example, if you enter mail.domain2.com, any users you add to the virtual host will receive mail at user@mail.domain2.com. 5 In the Aliases text box, specify alternate host names for which the server will accept mail. For example, if your mail host name is mail.domain2.com, you can set an alias of domain2.com so that IMail Server accepts mail addressed to fred@mail.domain2.com and also fred@domain2.com. Multiple aliases are separated by a space. This field is limited to 255 characters. 6 For the Top Directory Name text box, enter the name of the directory where the directories for users, lists, and web files for this virtual host will be stored. In most cases, you will use a different directory for each virtual host. It is possible for virtual hosts to share a directory but then users that have the same names will actually share the same mailbox. 22

39 Configuration CHAPTER 2 7 Select the type of user database to use for this host. Use IMail User Database Use Local NT User Database Use External User Database For a description of these options, see User Registration and Authentication in the IMail Server Getting Started Guide. 8 Enter the default parameters for mailboxes and messages using the following options. These parameters apply to all users on the virtual host. For detailed information on each option, see Additional Host Settings on page 24. Default Max Mailbox Size. Default maximum size in bytes (characters) for the total of all mailboxes in a user s account. Default Max Messages. Default maximum number of messages (the total for all mailboxes) that will be allowed in a user s account. Single Message Max Size. Default maximum size (in bytes) for a single message sent to the server. Note: Each virtual host (domain) has an independent Single Message Max Size setting. However, the value configured for the domain bound to the IP address to which SMTP client connects to may override the Single Message Max Size setting configured for the virtual host. For example, if the host bound to the IP address that the client connects to for delivery has a 5 MB max setting and the virtual domain that the client is sending to has a 10 MB max setting, IMail's SMTP service will not accept a message larger than 5 MB. IMail Web Messaging, however, accepts messages based solely on the Single Message Max Size setting of the local destination domain. Maximum User Count. Maximum number of users that can be registered for the host. Note: The Maximum User Count does not apply to virtual hosts that are based on the Windows NT user database or an external database. Furthermore, the displayed counts of users for hosts that use the NT user database or an external database may not be correct. 9 Click Save, and then click Exit. After you have created the virtual host, you must add user mail accounts. For information on creating and modifying user mail accounts, See Working with User Accounts on page

40 CHAPTER 2 Configuration Additional Host Settings Once the virtual host has been configured, it appears in the left panel. Selecting the virtual host in the left panel, displays the host s General tab in the right panel as shown below. You can use this tab to alter the settings configured during the creation of the virtual host, and to access additional settings. The following options are available on this tab; the first two are not editable: Official Host Name. The name that is used to address mail to the users on the mail host. TCP/IP Address. The real or virtual IP address of the mail host. Top directory. The name of the directory where the directories for users, lists, and web files for this host are stored. Host Aliases. Alternate host names for which the host will accept mail. For example, if the mail host name is mail.domain2.com, you can set an alias of domain2.com so that IMail Server accepts mail addressed to fred@mail.domain2.com and also fred@domain2.com. Multiple aliases are separated by a space. Default Max Mailbox Size. The default maximum size, in bytes, for the total of all mailboxes in a user s account. If the total size exceeds the maximum, new mail is returned to the sender. Enter zero for an unlimited size. 24

41 Configuration CHAPTER 2 This value is the default limit used when the Max Mailbox Size value, for a user s account, is set to zero. Changing this value automatically changes the limit for all user accounts, on the host, that have zero for the Max Mailbox Size value. Otherwise, the user s Max Mailbox Size value will override. Single Message Max Size. The maximum size, in bytes, of a single message, with zero being unlimited. Messages that exceed this size are returned to the sender. Max Outbound Msg Size. The maximum size, in bytes of an outbound message. Messages larger than this size are bounced. Full Mailbox Notify%. If a value is entered, users are notified when their mailbox is within a certain percentage of being full. For example, if 80 is entered, users receive an when their mailbox is 80% full. Users get a maximum of one message a day, for three days. The message sent to the user is configurable. The text for this message can be customized by creating a Notify.txt file which should be placed in the top directory of the domain. If there is no Notify.txt file, the notification will contain the following standard text: User<!--imail.user--> Host <!--imail.host--> Your mailbox is nearly full, please remove some messages. If you have any questions, see your system administrator. The two tags will be replaced with the user ID and the domain. Full Mailbox Notify Address. The address of an additional address where an is sent when a user's mailbox is almost full. For example, this could be the system administrator s address. Default Max Messages. The default maximum number of messages (total for all mailboxes) that is allowed in a user s account. If the maximum is exceeded, any new mail is returned to the sender. Enter zero for an unlimited number. This value is the default limit used when the Max Messages value for the user s account is zero. Changing this value automatically changes the limit for all accounts on the host that have zero for their Max Mailbox Msgs value. Otherwise, the user s Max Mailbox Msgs value overrides the value entered here. Max Users. The maximum number of users that can be registered for this mail host. Enter zero for an unlimited number. The box next to this setting displays the number of users that exist on the host including the root user. Note: This setting does not apply to virtual domains that use the NT user database. The displayed counts of users for domains that use the NT user database may not be correct. Disable IM (displayed if Ipswitch Instant Messaging server is installed). This option allows you to disable Ipswitch Instant Messaging for the domain. To use this option, Ipswitch Instant Messaging must be configured to use the IMail database. Instant Messaging can also be disabled for each user on the user s General tab. 25

42 CHAPTER 2 Configuration Virus Scanning (displayed if IMail Anti-Virus is installed). Allows you to enable and disable virus scanning for the current domain. Sub-mailbox Creation. Allows administrators to specify what to do when a message arrives for a user and is addressed to a sub-mailbox which does not exist. Select one of the following actions: Create. Creates the sub-mailbox and delivers the message. Send to Inbox. Does not create the sub-mailbox, instead the message is delivered to the "main" mailbox. Bounce. Bounces the mail as an invalid user. In the User Database Type area, select one of the following: IMail Database NT Database External Database Adding Hosts Based on External Databases IMail Server can use an external database to register and authenticate users on a particular mail host. Users that you add to and delete from an IMail Server host are also added to and deleted from the external database. Before you use an external database for a mail host, use the Windows Control Panel to make sure there is a System DSN (Data Source Name) that points to a valid database name. See your Windows and database documentation for information on the System DSN. After you have verified the System DSN that points to the database you want to use, the next step depends on whether you are creating a new primary host or converting an existing host to an external database. Configuring the Primary Host If you have installed IMail Server for the first time, and have based the primary host on an external database, you are ready to configure the host. 1 Start IMail Administrator and select localhost in the left panel. 2 Click Add Host. 3 Select the primary host in the list. 4 Click Configure. Go to Configuring an External User Database on page

43 Configuration CHAPTER 2 Creating a Host Based on an External Database 1 Start IMail Administrator and select localhost in the left panel. 2 The General tab appears, in the right panel. Click Add Host. The Virtual Host Configuration dialog appears. 3 Click Add. A virtual host name (i.e. $virtual001) appears in the Local Addresses list. 4 Select Use External User Database. 5 Click Save. 6 Click Configure. The External User Database dialog box appears. Go to Configuring an External User Database on page 27. Configuring an External User Database The connection between IMail Server and an external user database is accomplished via a dynamic link library (DLL file). IMail Server includes a sample.dll file (ODBCUSER.DLL). This DLL uses the ODBC method, but can be modified to support other external database methods. The complete source code for this DLL is provided upon request from Ipswitch. When you configure an external user database, IMail Server creates an ODBC database that holds tables configured with the correct fields. The fields are identified in the Table Name section below. After the database is created and the ODBC system data source name is established in the ODBC Source Administration tool (located in the Windows Control Panel), you can use the database to store user authentication information and user properties. This information can be managed through IMail Administrator, including adding and deleting users. Note: When you use an external database, any IMail service you run (except the System Logger Service) must be set up (using the Control Panel Services application) so the account that IMail Server runs under has access to the external database. 27

44 CHAPTER 2 Configuration To configure an external database connection: 1 Follow the instructions in Creating a Host Based on an External Database on page In the Virtual Host Configuration dialog box, select Use External User Database, then click Configure. The External User Database dialog box opens. 3 Enter the parameters for the external user database: External Database Implementation DLL. Enter the full path to the odbcuser.dll installed on your local server or the path of a.dll that supports the functions: GetUserEntry, SetUserEntry, DeleteUserEntry, AuthorizeUser, GetFirstUserEntry, and GetNextUserEntry. (These are defined in the odbcuser.h file.) ODBC System Data Source Name (DSN). Enter the source name for the database where the user information is stored. IMAILSECDB is the default name that the ODBC link uses. Note: For users using SQL 7.0 or above, enter the following information after the ODBC System Data Source Name box: DNS_NAME;UID=<username>;PWD=<password>. The user name and password need to be the user ID and password for the SQL database and not an IMail Server account. Example: If you use the Data Source Name IMAILSECDB and the username AUGUSTA and password GEORGIA, the correct format of the ODBC System Data Source Name box is: IMAILSECDB;UID=AUGUSTA;PWD=GEORGIA 28

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