SMTP training course description

A hands on course focusing on the workings of email systems and the standard protocols that they use. The course is not specific to any particular implementation, but some vendor specifics are noted. Linux and Microsoft machines are used in hands on sessions to reinforce the theory of major sessions. The course concentrates on troubleshooting and interworking using network sniffing and protocol inspection rather than "which buttons to push".

What will you learn

• Describe and explain
  SMTP
  MIME
  POP3
  IMAP
  PGP, GPG, S/MIME
  SPF, DKIM, DMARC
• Configure mail routing
• Secure email systems

SMTP training course details

SMTP training course contents

• SMTP architecture

What is SMTP, email before SMTP, SMTP history, the different protocols, clients, servers. Email composition, transmission, delivering emails, storing and reading emails. MUAs, MTAs, POP3, IMAP, SMTP, DNS, webmail.
Hands on Setting up MTAs and MUAs and sending a simple email using telnet.

• The SMTP protocol

SMTP protocol stack, SMTP headers, HELO, SMTP mail, MAIL FROM, RCPT TO, DATA, SMTPUTF8, 8BITMIME, TURN, EHLO, ETRN, 3 digit replies.
Hands on Analysing SMTP packets on a network.

• DNS and SMTP

SMTP forwarding, SMTP relays, interoperation, how SMTP uses DNS, MX records.
Hands on Setting up mail relays.

• SMTP headers

IMF data, From, to, cc, bcc, sender and recipient headers, message Ids, received trails, in-reply-to, received-SPF, mail list headers.
Hands on Using clients to analyse details from mail headers, including true originators and path of emails.

• MIME

Email attachments, MIME versions, content type headers, encoding, base 64, binary data, multi part headers, troubleshooting attachments.
Hands on Analysing MIME headers and attachments.

• POP3

What is POP3, where to use POP3, authorisation, transactions, POP3 commands: USER, PASS, STAT, LIST, RETR, DELE.
Hands on Setting up a POP3 server, analysing POP3 packets on a network.

• IMAP and IMAPS

What is IMAP, where to use IMAP, authorisation, mailbox structure, IMAP commands: LOGIN, AUTHENTICATE, LIST, CREATE, Examine (message flags), SELECT, STORE.
Hands on Setting up an IMAP server and analysing IMAP packets on a network.

• Interoperation

Mail gateways, addressing, Exchange, sendmail.

• Email security

Basics, Transport level: STARTTLS. Content: PGP/GPG, mail signing and encryption, S/MIME, digital certificates, secure email submission.
Hands on Setting up and using a PGP key, configure MTAs to use TLS.

• Email authentication and spam prevention

Mail relays, grey listing, block list & RBL, DNSBL (Real-time Black hole List), White list, SPF, Domain Keys Identified Mail (DKIM), Author Domain Signing Practices (ADSP), Abuse Report Format (ARF), Domain-based Message Authentication, Reporting and Conformance (DMARC).
Hands on Relay spamming and the blocking spamming.

Learning path

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