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Securing Email

Learn about the protocols used for retrieving and sending email, such as POP, IMAP, and SMTP, and the importance of securing email communications through encryption and authentication methods.

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Securing Email

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  1. Securing Email Bruce Maggs

  2. Separate Suites of Protocols • Protocols for retrieving email: POP, IMAP, MAPI (Microsoft Exchange) • Protocols for sending email: SMTP

  3. POP (Post Office Protocol) • Current version is POP3, RFC 1939. • Client connects to POP server on port 110 • Originally, everything was sent in the clear. • Yes, everything, including user name, password, and your mail. • Now it’s common to connect instead to port 995 using SSL/TLS, same PKI as Web.

  4. POP3 Dialog S: <wait for connection on TCP port 110> C: <open connection> S: +OK POP3 server ready <1896.697170952@dbc.mtview.ca.us> C: USER mrose S: +OK User accepted C: PASS tanstaaf S: +OK Pass accepted C: STAT S: +OK 2 320 C: LIST S: +OK 2 messages (320 octets) S: 1 120 S: 2 200 S: . C: RETR 1 S: +OK 120 octets S: <the POP3 server sends message 1> C: QUIT S: +OK dewey POP3 server signing off (maildrop empty) C: <close connection> S: <wait for next connection>

  5. Experimenting with a POP3 Server telnet pop.example.com 110 openssl s_client -connect pop.example.com:995 -quiet

  6. APOP (RFC 1460) S: <wait for connection on TCP port 110> C: <open connection> S: +OK POP3 server ready <1896.697170952@dbc.mtview.ca.us> C: APOP mrose c4c9334bac560ecc979e58001b3e22fb S: +OK mrose's maildrop has 2 messages (320 octets) • 1896.697170952 is a time stamp • shared secret is the password "tanstaaf“ • Client applies MD5 algorithm to the string <1896.697170952@dbc.mtview.ca.us>tanstaaf • which produces a digest value of c4c9334bac560ecc979e58001b3e22fb • Password not sent in the clear, digest can’t be reused Other authentication methods include SASL and Kerberos.

  7. IMAP (Internet Message Access Protocol) • Current version is IMAP4, RFC 3501. • Client connects to IMAP server on port 143. • Originally, user name, password, mail sent in the clear. • Now connect to port 993 using SSL/TLS.

  8. IMAP Dialog S: * OK IMAP4rev1 Service Ready C: a001 login mrc secret S: a001 OK LOGIN completed C: a002 select inbox S: * 18 EXISTS S: * FLAGS (\Answered \Flagged \Deleted \Seen \Draft) S: * 2 RECENT S: * OK [UNSEEN 17] Message 17 is the first unseen message S: * OK [UIDVALIDITY 3857529045] UIDs valid S: a002 OK [READ-WRITE] SELECT completed C: a003 fetch 12 full

  9. More IMAP Authentication Mechanisms (RFC 1731) Kerberos, GSSAPI, S/Key (like APOP) Kerberos example: S: * OK IMAP4 Server C: A001 AUTHENTICATE KERBEROS_V4 S: + AmFYig== (random 32-bit number) C: BAcAQU5EUkVXLkNNVS5FRFUAOCAsho84kLN3/IJmrMG+25a4DT +nZImJjnTNHJUtxAA+o0KPKfHEcAFs9a3CL5Oebe/ydHJUwYFd WwuQ1MWiy6IesKvjL5rL9WjXUb9MwT9bpObYLGOKi1Qh (ticket and an authenticator for the principal "imap.hostname@realm") S: + or//EoAADZI= C: DiAF5A4gA+oOIALuBkAAmw== S: A001 OK Kerberos V4 authentication successful

  10. SMTP (Simple Mail Transfer Protocol) • Currently described in RFC 5321 • Client connects to SMTP server on port 25 • Originally everything was sent in the clear • Originally client could send mail without authenticating! *** SPAM *** ***FORGERY*** • Port 465 used for SSL/TLS • Sender’s SMTP server relays mail to receiver’s SMTP server • DNS Mail Exchanger (MX) records used to resolve mail domain name to IP address of SMTP server of recipient, e.g., bmm@cs.duke.edu

  11. DNS MX Record

  12. SMTP Dialog S: 220 smtp.example.com ESMTP Postfix C: HELO relay.example.org S: 250 Hello relay.example.org, I am glad to meet you C: MAIL FROM:<bob@example.org> S: 250 Ok C: RCPT TO:<alice@example.com> S: 250 Ok C: RCPT TO:<theboss@example.com> S: 250 Ok C: DATA S: 354 End data with <CR><LF>.<CR><LF> C: From: "Bob Example" <bob@example.org> C: To: "Alice Example" <alice@example.com> C: Cc: theboss@example.com C: Date: Tue, 15 January 2008 16:02:43 -0500 C: Subject: Test message C: C: Hello Alice. C: This is a test message with 5 header fields and 4 lines in the message body. C: Your friend, C: Bob C: . S: 250 Ok: queued as 12345 C: QUIT S: 221 Bye {The server closes the connection}

  13. STARTTLS Instead of using separate ports for SSL/TLS connections, POP, IMAP, SMTP connections can be converted from plain text to encryped communications through the use of the STARTTLS command. S: <waits for connection on TCP port 25> C: <opens connection> S: 220 mail.example.org ESMTP service ready C: EHLO client.example.org S: 250-mail.example.org offers a warm hug of welcome S: 250 STARTTLS C: STARTTLS S: 220 Go ahead C: <starts TLS negotiation> C & S: <negotiate a TLS session> C & S: <check result of negotiation> C: EHLO client.example.org

  14. SMTP AUTH Extension S: 220 smtp.example.com ESMTP Server C: EHLO client.example.com S: 250-smtp.example.com Hello client.example.com S: 250-AUTH GSSAPI DIGEST-MD5 S: 250-ENHANCEDSTATUSCODES S: 250 STARTTLS C: STARTTLS S: 220 Ready to start TLS ... TLS negotiation proceeds.Further commands protected by TLS layer ... C: EHLO client.example.com S: 250-smtp.example.com Hello client.example.com S: 250 AUTH GSSAPI DIGEST-MD5 PLAIN C: AUTH PLAIN dGVzdAB0ZXN0ADEyMzQ= S: 235 2.7.0 Authentication successful

  15. Warning! • Mail relayed between two SMTP servers might not be encrypted. • (Even if sender and recipient connect securely to their SMTP and IMAP servers.)

  16. SORBS (SPAM and Open-Relay Blocking System) • Database of bad SMTP (blacklisted) relays accessed through DNS • Mail won’t be accepted from these relays (Also SPAMHAUS database.)

  17. Proving your SMTP Relay is Legit • Register reverse DNS name • DKIM – relay signs headers with its private key, receiver can verify that relay is in the same domain (e.g., cs.duke.edu) as sender • SPF – list of which servers are permitted to originate email for which domains, accessed via DNS

  18. Signing Your Email • PGP (Pretty Good Privacy) • Certificate signed by certificate authority, e.g., Comodo.

  19. PGP • Developed by Phil Zimmerman • OpenPGP standard described in RFC 4880 • Public key bound to user name or email address • No centralized certificate authority in original design • Public keys can be signed by other users attesting to their authenticty, often at key-signing parties • Supported in Thunderbird, Pine, with plug-in in Outlook.

  20. Comodo • Verifies that you can receive email at the address that you want a certificate for.

  21. Retrieve Certificate • Chrome downloads and stores certificate.

  22. Install in Thunderbird • (easier if downloaded to Firefox than Chrome)

  23. My First Signed Message

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