LinuxCBT Mail Edition ( Sendmail, Postfix & qmail )

LinuxCBT Mail Edition focuses on the 3 leading Mail Transfer Agents (MTAs) and ancillary components:

Sendmail - LinuxCBT Sendmail Edition
Postfix - LinuxCBT Postfix Edition
qmail - LinuxCBT qmail Edition.

Linux/UNIX systems are responsible for moving the overwhelming majority of electronic mail across private and public networks. Consequently, savvy Systems Admins. are expected to have a solid foundation in MTAs and ancillary components for general and automated mail-based applications.

Let LinuxCBT Mail Edition help to solidify your understanding of key MTAs and ancillary components.

Recommended Prerequisites:

Familiarity with electronic mail concepts (MUA/MTA/etc.)
Access to a GNU/Linux-based PC to install the MTAs and ancillary components used

LinuxCBT Sendmail v8 Edition - Disc 1

Sendmail - Installation
Network & systems architecture review
Download current Sendmail v8.x.x source files
Import PGP-compatbile public keys
Verify source archive against imported public keys
Discuss required applications
Install GNU C Compiler (GCC) and ancillary applications
Backup existing Postfix implementation and prepare for Sendmail installation
Explore Sendmail source tree - identify key components
Configure & compile Sendmail
Discuss M4 & CF configuration files (sendmail.{mc,cf}, submit.{mc,cf})
Discuss default Sendmail operating modes - MSP & MTA
Prepare default Mail Submission Program (MSP) configuration based on MC
Prepare default Mail Transfer Agent (MTA) configuration based on MC
Install Berkeley DB libraries for hashed lookups
Complete installation
Explore post-installation Sendmail environment

Sendmail - Mail Submission Program (MSP) mode
Discuss local injection of messages
Explain required Sendmail MSP shell arguments for queue-runner mode
Start Sendmail in MSP mode
Verify Operating System (OS) results using BASH exit status
Verify monitored queue in MSP mode
Examine resultant Sendmail MSP Process Identification (PID) file creation
Kill running instance of Sendmail in MSP mode
Invoke Sendmail queue-runner mode
Inject test messages into the local queue
Examine the queue files generated by Sendmail MSP
Examine Syslog configuration using GREP
Discuss Sendmail logging
Identify Sendmail log files
Examine specific Sendmail log entries using GREP

Sendmail - Mail Transfer Agent (MTA) mode
Discuss Sendmail’s separation of duties; MSP/MTA
Explain required shell arguments for Sendmail MTA mode
Invoke Sendmail in MTA mode running as a daemon
Confirm Sendmail running in MTA mode
Force delivery of locally-injected messages
Confirm delivery of queued messages

Sendmail - Local Mail
Discuss Sendmail’s local delivery mechanism
Explore & discuss legacy /var/spool/mail directory
Identify user mbox files
Discuss mbox permissions
Illustrate local mail injection flow
Use mutt MUA to retrieve locally delivered mail
Use mutt to reply to envelope sender by local injection using MSP
Identify local mailer (procmail) used by Sendmail MTA
Invoke Sendmail in verbose mode
Attempt delivery to valid and invalid users & examine output
Explain Sendmail verbose-mode transcript (local vs. remote)

Sendmail - Logs
Discuss Syslog semantics (facilities & levels)
Discuss log rotation
Examine logs & discuss entries
Parse logs for interesting entries
Identify sourced messages
Discuss record types (receipt vs. delivery attempt(s))
Follow the message trail based on queue ID
Explain Sendmail fields
Identify PID related to various delivery attempts
Identify total delivery time and transfer time

Sendmail - Aliases
Discuss aliases applications
Identify aliases database
Explain Sendmail’s aliases expansion logic
Discuss the default aliases - (mailer-daemon, postmaster, etc.)
Test delivery to defined aliases
Define additional aliases
Rebuild aliases database using newaliases to route messages accordingly
Verify deliverablility of aliases database entries
Test delivery of messages to newly-defined aliases
Examine Sendmail logs to view transcript of delivery to aliased user
Explain the different types of supported Sendmail aliases
Define lists using aliases - one-to-many mappings
Test delivery to lists
Define alias to deliver messages to mbox-compliant file
Debug I/O errors related to Sendmail’s attempt to write to mbox-compliant file
Implement lists using file system includes
Define piped aliases to redirect messages to the input stream of other applications
Implement Sendmail’s per-user .forward file for user-based message routing
Setup aliases using pipes to the vacation program to enable auto-response

Sendmail - Simple Mail Transfer Protocol (SMTP) Mail
Discuss SMTP prerequisites
Examine local name resolution configuration
Confirm resolution of remote Sendmail server
Identify available remote recipients
Compose and deliver message to remote recipient
Confirm receipt
Reveal returned message headers using mutt MUA
Disable message forwarding on remote host
Confirm receipt of smtp-based messages
Explain Sendmail’s name resolution logic during delivery attempt
Emulate Sendmail’s name resolution logic to illustrate logic
Demonstrate Sendmail delivering messages based on static HOSTS resolution
Disable static name resolution for remote host
Debug message delivery errors related to invalid name resolution
Create DNS entry for remote server on primary DNS server
Confirm DNS resolution using system tools
Confirm mail delivery based on DNS resolution

Sendmail - Mail Exchange (MX) based messaging
Explain Sendmail’s name resolution logic
Use system tools to determine MX handler
Attempt delivery to undefined MX handler
Update DNS configuration to include MX & A records for second-level domain
Attempt delivery to defined MX handler
Confirm delivery based on MX resolution via logs and MUA
Explain MX distances (priority) field
Define additional MX host for second-level domain in DNS zone
Test delivery to backup MX host for failover

Sendmail - m4 Configuration Technique
Discuss Sendmail.cf
Explain advantages of using m4
Identify m4 templates in Sendmail source tree
Explain m4 templates hierarchy
Describe the structure of standard Sendmail m4-compliant files
Use m4 to generate new Sendmail.cf file
Increase logging verbosity
Reload current instance of Sendmail and examine output
Restrict the number of recipients
Restrict the size of each message
Use m4 to generate and test new configuration features
Sendmail - Masquerading
Discuss masquerading features and applications
Explore default Sendmail masquerading configuration using MUA
Alter Fully Qualified Domain Name (FQDN) of outbound messages using masquerading
Regenerate Sendmail.cf using m4 technique
Configure system to receive messages for new FQDN defined using masquerading
Alter message envelope using masquerading feature
Add Windows 2003 Host to DNS configuration & confirm resolution
Masquerade outbound domain to reflect second-level domain

Sendmail - Relay Control
Discuss Sendmail’s default relay rules
Configure promiscuous relay & test consequences
Relay mail to Internet-based host and confirm delivery using SSH
Restrict relaying by defining relay domains
Define & test file-based relay domains to permit hosts & subnets to relay
Recompile Sendmail.mc using m4 technique
Examine relaying with unresolvable domains
Confirm relay to Internet-based host using relay domains and Windows 2003 Host
Discuss benefits of using access db
Define mc directives for access db invocation
Create access db file using makemap
Explore access db directives
Discuss mailertable feature
Define mailertable with forced SMTP routes
Simulate DMZ-based MTA-front-end relaying messages to corporate back-end MTA
Test results
Confirm SMTP Auth pre-requisites
Configure SMTP Auth support
Recompile Sendmail to support SMTP Auth
Test relaying from Outlook Express on Windows 2003 Host

Sendmail - Smart Host Configuration
Discuss Smart Host applications
Configure Sendmail to use remote server as a Smart Host
Rebuild configuration files
Test local mail routing
Test smart host routing

Sendmail - Null Client Configuration
Discuss Null Client applications
Undefine Smart Host configuration
Configure Sendmail as a null client
Test mail routing as a null client
Confirm forced SMTP route

Sendmail - Virtual Domains
Explain applications
Define basic-global virtual domains applied to all mailboxes
Update DNS configuration to route messages to appropriate Virtual Domain server
Confirm delivery of messages to users at virtual domain
Add new DNS zone for additional domain to route traffic accordingly
Discuss virtual user tables applications
Updated Sendmail.cf to include virtual user tables support
Define virtual user domains hash
Define virtual user maps
Test delivery to various users at various domains
Define and test a catchall address for a virtual domain
Rebuild virtual user maps using makemap
Relay virtual domains to remote recipients

Sendmail - Malware Framework
Discuss Malware Framework (MailScanner/ClamAV/SpamAssAssin)
Dowload MailScanner
Download Clam Anti-Virus (ClamAV)
Download SpamAssAssin

Clam Anti-Virus (ClamAV)
Install requisite ClamAV components
Compile & install ClamAV
Identify key ClamAV binaries
Update ClamAV configuration files for basic operation
Update ClamAV definitions
Invoke ClamAV as a daemon

SpamAssAssin Installation
Identify requisite SpamAssAssin components
Compile & install SpamAssAssin
Invoke SpamAssAssin as a daemon

MailScanner Implementation
Compile & install MailScanner
Identify MailScanner-related directories
Explore MailScanner’s primary configuration
Enable ClamAV & SpamAssAssin support
Alter Sendmail queue configuration to support MailScanner
Restart Sendmail
Start MailScanner
Test message delivery through malware framework
Test sample Spam through malware framework
Test sample Virus-laden file through malware framework

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LinuxCBT Postfix Edition - Disc 2

Postfix - Installation
Identify a geographically close Postfix mirror location
Discuss Postfix nomenclature
Download Postfix
Import PGP-compatible key to verify downloaded source archive
Verify Postfix source archive against imported signature
Extract Postfix source archive
Identify existing system MTA configuration
Explore Postfix source tree
Discuss pre-requisites
Identify Sendmail-compatible binaries to backup
Add required Postfix user and groups
Compile & install Postfix
Identify key directories and binaries
Alter key Postfix configuration files for basic operation

Postfix - Local Mail & Queueing
Define local domains in main configuration file
Define Fully Qualified Domain Name (FQDN) of Postfix Host
Confirm running Postfix TCP (super server) Manager
Explore current running directives with postconf
Alter configuration to enable local aliases
Use sendmail-compatible binary to inject messages into the local queue
Confirm delivery via default Syslog location
Identify default mbox-based mailstore
Use MUA mutt to verify delivery of local mail
Discuss & explore various Postfix queues
Explain how Postfix implements local injection
Explain how Postfix handles SMTP-based mail

Postfix - Aliases
Discuss concepts and applications for aliases
Identify required aliases
Describe Sendmail-compatible alias types
Define 1-to-1 aliases
Define list-based aliases
Test aliases delivery
Discuss per-user aliases (.forward) file
Define per-user .forward file with redirection to vacation program
Test delivery and auto-response
Discuss how mail is routed into the file system (maildrop) while Postfix is up/down
Identify binaries responsible for local mail injection (pickup/cleanup)

Postfix - Simple Mail Transfer Protocol (SMTP)
Confirm the existence of remote recipients
Inject mail for delivery to remote Linux Host
Review Postfix delivery report generated upon invocation of verbose mode
Confirm delivery of remote mail to remote Linux Host
Use MUA mutt to reveal and explore the headers of SMTP-based mail
Explore name resolution order file & discuss logic
Configure Postfix to receive mail to second-level domain plus FQDN
Simulate Postfix name resolution process at delivery-time
Expose current Mail Exchanger (MX) Host for the second-level domain

Postfix - Rewriting Features - Canonical Maps - BCC Maps
Discuss default configuration
Examine envelope headers
Configure Postfix to masquerade outbound messages
Test masqueraded envelope by generating new mail
Discuss canonical maps concepts & applications
Explain corresponding rewrite binaries
Define canonical maps in Ascii format
Use Postmap to generate DB-formatted canonical maps
Instruct main.cf to employ canonical maps database
Test address rewriting using canonical maps
Confirm message delivery via Syslog-generated logs
Examine the headers of delivered message altered using canonical maps & myorigin
Define & test sender canonical maps
Define & test recipient canonical maps
Configure Postfix to BCC all messages to specified recipients
Test messages between various users to ensure BCC functionality
Configure Postfix to BCC messages based on specific senders
Define Sender BCC maps using editor and Postmap to generate Hashed DB

Postfix - Relay Control
Explore & discuss default relay behavior
Identify key relay-related directives
Connect to remote Windows 2003 Host and attempt to relay
Confirm DNS resolution of Postfix relay host
Attempt relay to recipient on relay host & confirm path via logs
Attempt relay to recipient on foreign host & confirm delivery
Tighten default Postfix relay policy to restrict relaying to local subnet
Attempt local subnet and Internet-based relays & confirm results
Use SMTP commands to expose features supported by Postfix MTA
Discuss SMTP Auth pre-requisites
Recompile Postfix to support SMTP Auth
Configure Postfix with SMTP Auth to restrict relaying by users vs. IP or hostname
Confirm support of SMTP Auth using standard STMP commands
Configure Outlook Express client to support SMTP Auth
Attempt to relay based on SMTP Auth support
Permit relaying of non-local domains based on relay domains
Define additional second-level domain for relaying
Configure relaying of non-local domains using hashed Berkeley DB maps
Discuss Postfix transport maps concepts and applications
Define transport maps for domains to bypass DNS MX lookups
Update receiving Postfix host to support transport maps
Confirm delivery of messages to additional domains defined in transport maps
Configure Postfix as a Backup Mail Exchanger (MX) host and confirm delivery during failure

Postfix - Smart Host & Null Client configuration
Discuss Smart Host concepts and applications
Define the Postfix Smart Host
Define the Postfix Smart Host client
Test local delivery and confirm delivery
Test delivery of Internet-based message which requires Smart Host
Confirm delivery via logs and remote SSH session
Discuss Null client concepts and applications
Internet -> DMZ -> Corporate Backbone Mail Repository
Disable local mail delivery on Postfix host
Configure Postfix to function as a null client
Test results of null client delivery

Postfix - Virtual Domains
Discuss default domains handled by Postfix
Attempt IP-address based delivery
Explore the mydestination parameter
Alter BIND configuration to route messages for basic virtual domain
Configure Postfix to map individual users to domains
Define individual virtual domains hash
Define virtual domains user hash
Generate hashed virtual domains and virtual user databases
Confirm routing of messages to appropriate users
Define catchall addresses for non-matching users and/or aliases
Use Postmap to query virtual users and determine delivery path

Postfix - Mailbox Formats
Explore default mbox configuration location and permissions
Describe mbox format
Explore environment configuration variables related to mail delivery
Test delivery of mbox-bound messages using mutt & Postfix
Discuss Maildir message storage format
Configure Postfix to deliver messages using Maildir message format
Examine Postfix-created Maildir structure after mail delivery
Alter shell environment to support Maildir format with desired MUA

Postfix - Network-based Mail Retrieval
Discuss Courier IMAP framework
Identify and install pre-requisites
Download, compile, and install Courier Authentication Library Daemon
Identify Courier Authentication key directories, binaries and configuration file
Download and install Courier IMAP Daemon
Explore Courier IMAP binary directory tree
Discuss Courier framework
Configure Courier for POP3 mail retrieval
Confirm retrieval using Windows 2003 - Outlook Express client
Identify POP3 Secure configuration files
Generate self-signed certificate for use with POP3 Secure communications
Confirm retrieval of messages using Outlook Expres and POP3 Secure
Establish run-level symbolic links for POP3 & POP3S services
Configure Courier for IMAP mail retrieval
Confirm retrieval using Windows 2003 - Outlook Express client
Generate self-signed certificate for use with IMAP Secure communications
Establish run-level symbolic links for IMAP & IMAPS services

Postfix - Web-based Mail Retrieval
Discuss Web-based SquirrelMail pre-requisites
Enable Apache web server
Download and Install SquirrelMail into web-accessible location
Secure data and attachments directories
Configure SquirrelMail for initial use with Courier IMAP
Address PHP session-related issues
Explore SquirrelMail from the browser as various Linux users
Confirm deliver using multiple clients - (mutt/Outlook Express/SquirrelMail/Local Injection)

Postfix - Malware Framework
Dowload MailScanner
Download Clam Anti-Virus (ClamAV)
Download SpamAssAssin
Download, compile & install zlib

Clam Anti-Virus (ClamAV) Implementation

Create required user and group

Compile & install ClamAV

Identify key ClamAV binaries

Update ClamAV configuration files for basic operation

Update ClamAV definitions

Configure system Crontab to update virus definitions every hour
Confirm scheduled virus definition updates 24 hours later

SpamAssAssin Implementation
Illustrate message flow from remote SMTP system through our Malware Framework
Download SpamAssAssin from Apache Foundation
Extract & discuss SpamAssAssin source tree
Compile and install Perl-based SpamAssAssin

MailScanner Implementation
Download, compile and install the current MailScanner malware engine
Explore MailScanner source and binary trees
Explore MailScanner.conf configuration file - discuss important directives
Update MailScanner to support Postfix MTA
Configure Postfix MTA to route inbound messages into temporary queue for processing
Invoke MailScanner malware engine and confirm
Debug incidentals related to invalid configuration directives and missing components
Malware Framework - MUA -> MTA -> MailScanner -> ClamAV -> SpamAassAssin -> MTA -> Maildir/Mailbox
Send sample malware through the malware framework & confirm detection
Send sample spam through the malware framework & confirm detection
Configure MailScanner to affix outbound Corporate Signatures - Legalise - to all messages based trusted configuration

Postfix - Log Analysis
Download AWStats log analysis application
Configure AWStats to function in current Apache Web Server environment
Discuss AWStats features and applications
Configure AWStats to process Postfix MTA Logs
Explore AWStats’ web-based interface

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LinuxCBT qmail Edition - Disc 3

qmail - Installation
Identify current Mail Transfer Agent (MTA) environment on Red Hat Enterprise box
Discuss system initialization environment
Disable current MTA in applicable run-levels
Identify qmail pre-requisites
Setup qmail source-tree hierarchy for build process
Discuss qmail’s modular, component architecture - relevant binaries
Navigate to a close qmail mirror
Download qmail components
Extract primary qmail packaged and dicuss contents
Patch original qmail sources
Install ucspi-tcp - INETD/XINETD substitute
Install dameontools - daemon management for qmail daemons
Create requisite users and groups
Compile and install qmail
Define default qmail environment
Explore and discuss the important qmail directories, symlinks and binaries
Illustrate internal qmail communications required for local and remote deliveries
Identify initial qmail startup process
Define genersal startup scripts for qmail
Define supervise scripts for qmail delivery
Define supervise scripts for qmail logging
Backup default local queue-injection process (Sendmail)
Create Sendmail symlink to qmail-compatible binary for local queue-injection
Start qmail & confirm processes and network bindings

qmail - Local Mail
Define required system aliases using qmail files
Configure qmail rules to permit local relaying
Identify default mbox mail storage format
Use MUA mutt to deliver mail via qmail
Examine delivery via qmail logs
Identify mbox destination
Discuss local queue-injection logic - qmail-inject/Sendmail
Explain permissions used by qmail when delivering local mail
Update local user’s environment variables and confirm message delivery
Identify variables used for local queue-injection
Explore and discuss the mbox mail storage format
Update global environment configuration to reflect new mbox storage location
Examine running qmail statistics
Inject messages into the queue of a downed MTA
Examine results
Explore a message’s path throught the local queue
Resume message delivery

qmail - Mail Storage Formats
Switch qmail global configuration from mbox to Maildir storage format
Use maildirmake to create Maildir-compliant directory structure for users
Explore standard Maildir directory tree
Restart qmail and attempt delivery to Maildir mailbox
Confirm deliver of message to Maildir recipient
Discuss Maildir file nomenclature
Update environment variables to reflect Maildir mail storage format
Explore headers of delivered messages and discuss key components

qmail - Aliases
Explain the benefits of aliases
Explore traditional Sendmail-style aliases in /etc/aliases
Compare and contrast Sendmail-style aliases to qmail-style (.qmail) aliases
Discuss key qmail alias user
Explore system-wide qmail aliases
Test delivery to system-wide qmail aliases
Define an abuse qmail-style alias and confirm delivery
Deine one-to-many qmail-style abuse alias and confirm delivery
Attempt delivery to non-existing local user or alias using Sendmail and confirm results
Define a catch-all system-wide alias to handle non-existing local users or accounts
Test catch-all system-wide alias by injecting messages bound to non-existing mailboxes
Discuss sub-addresses/address extensions using qmail aliases
Define sub-address for non-privileged user and confirm delivery using MUA mutt
Forward defined non-privileged sub-address to other local user and examine results
Redirect the abuse alias to a Mailbox-style repository for evidence-collection
Confirm appended alias-redirection of messages destined to catch-all accounts

qmail - Remote Mail
Identify key qmail daemons and binaries responsible for remote delivery
Explain remote delivery logic using DNS
Connect (SSH) to remote Linux system to be used for initial remote delivery & explore
Attempt remote delivery using qmail and FQDN of remote box and examine the qmail queue
Alter remote Postfix environment to find Maildir mailbox and confirm delivery using mutt
Update remote Postfix configuration to handle messages destined to second-level domain
Alter remote Postfix transport (smtproutes) file to disable static delivery
Confirm DNS second-level Mail Exchanger (MX) configuration for linuxcbt.internal domain
Attempt MX-based delivery and confirm delivery on remote host
Discuss employed qmail logic
Switch primary Mail Exchanger (MX) from Postfix box to qmail box - adjusting distances
Confirm MX distances using Domain Information Groper (dig)
Attempt delivery to second-level domain from the qmail box & confirm delivery
Explore qmail log files for message-delivery information
Debug qmail-smtpd delivery issues and adjust to ensure delivery
Discuss a Backup MX configuration for a given domain
Update DNS configuration to reflect the ideal MX distances
Confirm DNS configuration from a tertiary Linux server
Purposely fail the primary Postfix server for the linuxcbt.external domain
Configure qmail to be a Backup MX server for a business partner’s domain
Attempt delivery to the linuxcbt.external domain from the tertiary Linux server
Examine queued messages for the linuxcbt.external backup domain on the qmail box
Re-enable the primary domain’s Postfix box
Flush the qmail queue and examine delivery to the primary MX host

qmail - Relay Control
Discuss Smart Host applications
Explore pre-Smart Host SMTP delivery of messages to Internet-based host
Configure qmail to use a remote Postfix SMTP Smart Host system
Disable Smart Host configuration
Discuss qmail’s default relay policy
Identify key qmail configuration files related to relaying
Attempt to relay from a remote Windows 2003 Host through the open qmail MTA
Confirm delivery of message via qmail in open-relay mode to local and remote recipients
Secure open relay and confirm inability to relay messages to untrusted domains
Configure selective relaying based on individual host and subnet
Discuss the benefits of SMTP Auth
Explain qmail’s SMTP Auth implementation
Identify SMTP Auth pre-requisites
Download, compile and install CheckPassword authentication application
Debug compilation-related errors
Download SMTP Auth patch
Patch qmail sources and recompile to produce modified qmail-smtpd binary
Install new qmail-smtpd binary and prepare run scripts for usage
Attempt to relay with tightened relay permissions and confirm failure
Confirm SMTP Auth from Windows 2003 Host using Outlook Express
Relay outbound messages using SMTP Auth from Outlook Express client

qmail - Network-based Mail Retrieval
Discuss Mail retrieval authentication framework using Courier
Identify pre-requisites
Download, compile and install Courier Authentication Daemon

Identify Courier Authentication key directories, binaries and configuration file
Download and install Courier IMAP Daemon
Explore Courier IMAP binary directory tree
Discuss Courier framework
Configure Courier for POP3 mail retrieval
Confirm retrieval using Windows 2003 - Outlook Express client
Identify POP3 Secure configuration files
Generate self-signed certificate for use with POP3 Secure communications
Confirm retrieval of messages using Outlook Expres and POP3 Secure
Establish run-level symbolic links for POP3 & POP3S services
Configure Courier for IMAP mail retrieval
Confirm retrieval using Windows 2003 - Outlook Express client
Generate self-signed certificate for use with IMAP Secure communications
Establish run-level symbolic links for IMAP & IMAPS services

qmail - Web-based Mail Retrieval
Discuss Web-based SquirrelMail pre-requisites
Enable Apache web server
Download and Install SquirrelMail into web-accessible location
Secure data and attachments directories
Configure SquirrelMail for initial use with Courier IMAP
Address PHP session-related issues
Explore SquirrelMail from the browser as various Linux users
Confirm deliver using multiple clients - (mutt/Outlook Express/SquirrelMail/Local Injection)

qmail - Virtual Domains
Discuss qmail virtual domains support via system-wide aliases
Configure basic/global virtual domains using .qmail files
Confirm delivery to users @ virtual domains
Configure individual virtual domains
Confirm delivery to individuals @ virtual domains
Ensure non-global delivery to virtual domains
Define non-privileged user-managed virtual domains
Confirm deliver to user-managed virtual domains

qmail - Malware Framework - OpenProtect, Bad Senders, TLS
Discus the OpenProtect Malware Framework
Identify pre-requisites
Download OpenProtect
Install Open Protect
Explore OpenProtect Configuration (MailScanner/ClamAV/SpamAssAssin)
Configure outbound signatures
Configure qmail to reject users based header information
Confirm rejection from Windows 2003 Host - Outlook Express
Discuss Transport Layer Security framework and requirements
Implement Transport Layer Security (TLS)
Configure Outlook Express client to use TLS & test outbound relaying

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