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Syllabus

Focus: Sendmail Version 8x MTA

Duration: 14-Hours

  • LinuxCBT Sendmail v8 Edition - Module I

    • 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
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    • 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
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    • 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
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    • 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)
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    • 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
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    • 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
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    • 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
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    • 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 MXA 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • Sendmail - Malware Framework
      • Discuss Malware Framework (MailScanner/ClamAV/SpamAssAssin)
      • Dowload MailScanner
      • Download Clam Anti-Virus (ClamAV)
      • Download SpamAssAssin
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      • 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
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      • SpamAssAssin Installation
        • Identify requisite SpamAssAssin components
        • Compile & install SpamAssAssin
        • Invoke SpamAssAssin as a daemon
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      • 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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    • Sendmail - Transport Layer Security (TLS) Configuration
      • Discuss features & benefits
      • Discuss clear-text implications & caveats
      • Generate mail as a TLS client
      • Confirm one-way encryption
      • Generate PKI usage keys
      • Configure & confirm TLS Server support
      • Generate message responses
      • Confirm bi-directional encryption
      • Evaluate results
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LinuxCBT SendMail Edition

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DEMO