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Email: Beyond the send button

Email: Beyond the send button

A guide to what happens after you hit the send button on an email

Daniel Knell

January 25, 2016
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  1. Saying Hello 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here, nice

    to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n
  2. Is this line secure? 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com

    here, nice to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n
  3. Is this line secure? 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com

    here, nice to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n
  4. Is this line secure? 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com

    here, nice to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ]
  5. Lets start over… 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here,

    nice to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n
  6. Lets start over… 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here,

    nice to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n 250-mail.example.com here, nice to meet you bob.example.com\n 250 AUTH PLAIN LOGIN\n
  7. Papers please 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here, nice

    to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n 250-mail.example.com here, nice to meet you bob.example.com\n 250 AUTH PLAIN LOGIN\n AUTH LOGIN\n
  8. Papers please 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here, nice

    to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n 250-mail.example.com here, nice to meet you bob.example.com\n 250 AUTH PLAIN LOGIN\n AUTH LOGIN\n 334 VXNlcm5hbWU6\n
  9. Papers please 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here, nice

    to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n 250-mail.example.com here, nice to meet you bob.example.com\n 250 AUTH PLAIN LOGIN\n AUTH LOGIN\n 334 VXNlcm5hbWU6\n Ym9iQGV4YW1wbGUuY29t\n
  10. Papers please 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here, nice

    to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n 250-mail.example.com here, nice to meet you bob.example.com\n 250 AUTH PLAIN LOGIN\n AUTH LOGIN\n 334 VXNlcm5hbWU6\n Ym9iQGV4YW1wbGUuY29t\n 334 UGFzc3dvcmQ6\n
  11. Papers please 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here, nice

    to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n 250-mail.example.com here, nice to meet you bob.example.com\n 250 AUTH PLAIN LOGIN\n AUTH LOGIN\n 334 VXNlcm5hbWU6\n Ym9iQGV4YW1wbGUuY29t\n 334 UGFzc3dvcmQ6\n cGFzc3dvcmQ=\n
  12. Papers please 220 mail.example.com SMTP\n EHLO bob.example.com\n 250-mail.example.com here, nice

    to meet you bob.example.com\n 250-AUTH PLAIN LOGIN\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO bob.example.com\n 250-mail.example.com here, nice to meet you bob.example.com\n 250 AUTH PLAIN LOGIN\n AUTH LOGIN\n 334 VXNlcm5hbWU6\n Ym9iQGV4YW1wbGUuY29t\n 334 UGFzc3dvcmQ6\n cGFzc3dvcmQ=\n 235 Authentication succeeded\n
  13. Sending a message MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n
  14. Sending a message MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n \n
  15. Sending a message MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n \n What up dan? I’m just keeping it bob.\n - Bob\n
  16. Sending a message MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n
  17. Sending a message MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n 250 message queued\n
  18. Bye Bye MAIL FROM: [email protected]\n 250 ok\n RCPT TO: [email protected]\n

    250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n 250 message queued\n QUIT\n
  19. Bye Bye MAIL FROM: [email protected]\n 250 ok\n RCPT TO: [email protected]\n

    250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n 250 message queued\n QUIT\n 221 goodbye!\n
  20. MX Records $ dig MX danielknell.co.uk danielknell.co.uk. 3571 IN MX

    1 aspmx.l.google.com. danielknell.co.uk. 3571 IN MX 5 alt1.aspmx.l.google.com. danielknell.co.uk. 3571 IN MX 5 alt2.aspmx.l.google.com. danielknell.co.uk. 3571 IN MX 10 alt3.aspmx.l.google.com. danielknell.co.uk. 3571 IN MX 10 alt4.aspmx.l.google.com.
  21. Passing it on 220 mx.google.com ESMTP i2si23053074wja.89 - gsmtp\n EHLO

    mail.example.com\n 250-mx.google.com at your service, mail.example.com\n 250 STARTTLS\n
  22. Passing it on 220 mx.google.com ESMTP i2si23053074wja.89 - gsmtp\n EHLO

    mail.example.com\n 250-mx.google.com at your service, mail.example.com\n 250 STARTTLS\n STARTTLS\n
  23. Passing it on 220 mx.google.com ESMTP i2si23053074wja.89 - gsmtp\n EHLO

    mail.example.com\n 250-mx.google.com at your service, mail.example.com\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n
  24. Passing it on 220 mx.google.com ESMTP i2si23053074wja.89 - gsmtp\n EHLO

    mail.example.com\n 250-mx.google.com at your service, mail.example.com\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ]
  25. Passing it on 220 mx.google.com ESMTP i2si23053074wja.89 - gsmtp\n EHLO

    mail.example.com\n 250-mx.google.com at your service, mail.example.com\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO mail.example.com\n
  26. Passing it on 220 mx.google.com ESMTP i2si23053074wja.89 - gsmtp\n EHLO

    mail.example.com\n 250-mx.google.com at your service, mail.example.com\n 250 STARTTLS\n STARTTLS\n 220 Go ahead\n [ magical encryption stuff ] EHLO mail.example.com\n 250 -mx.google.com at your service, mail.example.com\n
  27. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n
  28. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n From: [email protected] To: [email protected] DKIM-Signature a=rsa-sha1; q=dns; d=example.com; [email protected]; s=example; c=relaxed/ simple; t=1117574938; x=1118006938; h=from:to:subject:date; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZVoG4ZHRNiYzR\n \n
  29. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n From: [email protected]\n To: [email protected]\n DKIM-Signature a=rsa-sha1; q=dns; d=example.com; [email protected]; s=foobar; c=relaxed/ simple; t=1117574938; x=1118006938; h=from:to:subject:date; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZVoG4ZHRNiYzR\n \n
  30. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n From: [email protected]\n To: [email protected]\n DKIM-Signature a=rsa-sha1; q=dns; d=example.com; [email protected]; s=foobar; c=relaxed/ simple; t=1117574938; x=1118006938; h=from:to:subject:date; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZVoG4ZHRNiYzR\n \n What up dan? I’m just keeping it bob.\n - Bob\n
  31. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n From: [email protected]\n To: [email protected]\n DKIM-Signature a=rsa-sha1; q=dns; d=example.com; [email protected]; s=foobar; c=relaxed/ simple; t=1117574938; x=1118006938; h=from:to:subject:date; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZVoG4ZHRNiYzR\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n
  32. DKIM Recod $ dig TXT foobar._domainkey.example.com foobar._domainkey.example.com. 2607 IN TXT

    "v=DKIM1\; k=rsa\; p=MIGfMA0GCSqGSIb3DQEBAQUAA4GNADCBiQKBgQCXBN08ApG6sfTDR0CQlmQ2aSEaaHnyux7HAv3AmKeKkUycvy1 SiT2bM6HJqozV+MkEi4Ut+tHm0OkTx4d4DyX7rT0pI6nJ6R75calBpT+h/ pTC1TWrY8C0CIxutlwBKgeJxbJmXVvW/g9PdaLMREITMizTOS3dXxoOJdWj/SRjwwIDAQAB"
  33. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n From: [email protected]\n To: [email protected]\n DKIM-Signature a=rsa-sha1; q=dns; d=example.com; [email protected]; s=foobar; c=relaxed/ simple; t=1117574938; x=1118006938; h=from:to:subject:date; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZVoG4ZHRNiYzR\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n 250 message queued\n
  34. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n From: [email protected]\n To: [email protected]\n DKIM-Signature a=rsa-sha1; q=dns; d=example.com; [email protected]; s=foobar; c=relaxed/ simple; t=1117574938; x=1118006938; h=from:to:subject:date; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZVoG4ZHRNiYzR\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n 250 message queued\n QUIT\n
  35. Passing it on MAIL FROM: [email protected]\n 250 ok\n RCPT TO:

    [email protected]\n 250 ok\n DATA\n 354 Start mail input; end with <CRLF>.<CRLF>\n Subject: Bobbing it up\n From: [email protected]\n To: [email protected]\n DKIM-Signature a=rsa-sha1; q=dns; d=example.com; [email protected]; s=foobar; c=relaxed/ simple; t=1117574938; x=1118006938; h=from:to:subject:date; b=dzdVyOfAKCdLXdJOc9G2q8LoXSlEniSbav+yuU4zGeeruD00lszZVoG4ZHRNiYzR\n \n What up dan? I’m just keeping it bob.\n - Bob\n .\n 250 message queued\n QUIT\n 221 goodbye!\n
  36. Useful terms • SMTP (Simple Mail Transfer Protocol) • SPF

    (Sender Policy Framework) • DKIM (Domain Keys Identified Mail) • DMARC (Domain-based Message Authentication, Reporting & Conformance)