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Lifecycle of an Email The care and feeding of electronic communications in their natural habitat.
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Transcript of Lifecycle of an Email The care and feeding of electronic communications in their natural habitat.
![Page 1: Lifecycle of an Email The care and feeding of electronic communications in their natural habitat.](https://reader035.fdocuments.us/reader035/viewer/2022062516/56649e2a5503460f94b18d40/html5/thumbnails/1.jpg)
Lifecycle of an Email
The care and feeding of electronic communications in their natural habitat
![Page 2: Lifecycle of an Email The care and feeding of electronic communications in their natural habitat.](https://reader035.fdocuments.us/reader035/viewer/2022062516/56649e2a5503460f94b18d40/html5/thumbnails/2.jpg)
Lifecycle of an Email
The cast of charactersFinding the trailRed herrings
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The Cast of Characters
Sending mail clientSMTP ServerMX ServerPOP3 / IMAP ServerReceiving mail client
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Supporting Cast
DNS sanity-checkingMTA-level blocklistsDCCClamAVLDSSpamAssassinGraymail
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The General Case
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Sonic.net to Sonic.net
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mail.sonic.net
Ports 25, 465, and 587SMTP AuthenticationSecure Password AuthenticationSTARTTLSSSMTP
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mail.sonic.net
Possible causes for rejectionUnauthenticated relayKnown-bad sender addressKnown-bad recipient domainDCC MatchVery poor SMTP behavior
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mail.sonic.net
Logs: /sonic-logs/mail/maillog.mail
Jun 18 08:00:37 b.mail.sonic.net sm-mta[8695]: l5IF0b2n008695: from=<[email protected]>, size=2565, class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA, relay=fw.office.sonic.net [209.204.177.119]
Jun 18 08:00:38 b.mail.sonic.net sm-mta[8702]: l5IF0b2n008695: to=<[email protected]>, delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=122565, relay=mailin-01.mx.sonic.net. [208.201.249.228], dsn=2.0.0, stat=Sent (l5IF0cgx029469 Message accepted for delivery)
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mx.sonic.net
Port 25 Over 2000 messages / minute average Domain aliases handled here
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mx.sonic.net
Possible causes for rejectionKnown-bad recipientOff-site relayMTA-level blocklistClamAVDCCDNS scrutinyVery poor SMTP behavior
![Page 12: Lifecycle of an Email The care and feeding of electronic communications in their natural habitat.](https://reader035.fdocuments.us/reader035/viewer/2022062516/56649e2a5503460f94b18d40/html5/thumbnails/12.jpg)
mx.sonic.net
Logs: /sonic-logs/mail/maillog.mxJun 18 08:00:38 e.mx.sonic.net sm-mta[29469]: l5IF0cgx029469:
from=<[email protected]>, size=2783, class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA, relay=b.mail.sonic.net [64.142.19.5]
Jun 18 08:00:38 e.mx.sonic.net sm-mta[29469]: l5IF0cgx029469: Milter add: header: X-Sonic-SB-IP-RBLs: IP RBLs .
Jun 18 08:00:38 e.mx.sonic.net sm-mta[29474]: l5IF0cgx029469: to=<[email protected]>, delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=122783, relay=lds.sonic.net. [208.201.249.231], dsn=2.0.0, stat=Sent (l5IF0c9N010294 Message accepted for delivery)
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lds.sonic.net
Local Delivery System.forward happens hereSpamAssassin happens hereProcmail happens here
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lds.sonic.net
Possible causes for rejectionJust about everything on the last slideFew proper bounces from lds
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lds.sonic.net
Logs: /sonic-logs/maillog.ldsJun 18 08:00:38 eth0.a.lds.sonic.net sm-mta[10294]: l5IF0c9N010294:
from=<[email protected]>, size=3013, class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA, relay=e.mx.sonic.net [208.201.249.228]
Jun 18 08:00:38 eth0.a.lds.sonic.net sm-mta[10295]: l5IF0c9N010294: [email protected], delay=00:00:00, xdelay=00:00:00, mailer=local, pri=153220, dsn=2.0.0, stat=Sent
Jun 18 08:00:39 eth0.a.lds.sonic.net sm-mta[10295]: l5IF0c9N010294: [email protected], delay=00:00:01, xdelay=00:00:01, mailer=local, pri=153220, dsn=2.0.0, stat=Sent
Jun 18 08:00:43 eth0.a.lds.sonic.net sm-mta[10295]: l5IF0c9N010294: [email protected], delay=00:00:05, xdelay=00:00:04, mailer=local, pri=153220, dsn=2.0.0, stat=Sent
Jun 18 08:00:43 eth0.a.lds.sonic.net sm-mta[10295]: l5IF0c9N010294: to=: [email protected],[email protected], delay=00:00:05, xdelay=00:00:00, mailer=esmtp, pri=153220, relay=mailin-02.mx.sonic.net. [209.204.159.4], dsn=2.0.0, stat=Sent (l5IF0hA6023556 Message accepted for delivery)
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lds.sonic.net
When SpamAssassin works:
Jun 18 14:12:45 eth0.b.lds.sonic.net sm-mta[32736]: l5ILCj5U032736: from=<[email protected]>, size=3520, class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA, relay=g.mx.sonic.net [64.142.100.90]
Jun 18 14:12:47 eth0.a.lds.sonic.net graymail: jdf sent <[email protected]> "Delois Sarah" <[email protected]> to graymail
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spam.sonic.net
Logs: /sonic-logs/mail/maillog.spam
Jun 18 14:12:42 eth0.d.spam.sonic.net spamd[2017]: spamd: processing message <[email protected]> for jdf:99
Jun 18 14:12:47 eth0.d.spam.sonic.net spamd[2017]: spamd: result: Y 5 - DKIM_POLICY_SIGNS OME,HTML_MESSAGE,MIME_HTML_ONLY,MONEY_BACK,RAZOR2_CF_RANGE_51_100,RAZOR2_CF_RANGE_E4_51_1 00,RAZOR2_CF_RANGE_E8_51_100,RAZOR2_CHECK,RDNS_NONE scantime=5.0,size=3759,user=jdf,uid=9 9,required_score=5.0,rhost=eth0.a.lds.sonic.net,raddr=208.201.249.231,rport=44935,mid=<[email protected]>,autolearn=disabled
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pop.sonic.net
Ports 110 & 995 Around 500 messages / minute
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Where did it go?
MTA-level
Blocklists
SpamAssassin
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pop.sonic.net
Logs: /sonic-logs/mail/popper
Jun 18 08:01:12 c.pop.sonic.net pop3d: LOGIN, user=jdf, ip=[::ffff:209.204.177.119]
Jun 18 08:01:12 c.pop.sonic.net pop3d: LOGIN, dir=/var/spool/mail/03/27/jdf
Jun 18 08:01:13 c.pop.sonic.net pop3d: LOGOUT, user=jdf, ip=[::ffff:209.204.177.119], top=0, retr=6786
Jun 18 08:01:13 c.pop.sonic.net pop3d: jdf 209.204.177.119 0.638754 276(Y) 2 (6786), 276 (1490804)
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Red Herrings
Not all mail goes through mxNot all activity on lds is loggedSome “missing” mail isn’t
BlocklistsAliasesForwardsGraymailMUA-level sorting
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Finding the Trail
Headers show most of the story
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Finding the Trail
A little different after Graymail
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Lifecycle of an Email
/sonic-logs/mail/maillog.mailJun 14 21:54:28 b.mail.sonic.net sm-mta[25018]: l5F4sSsY025018: from=<[email protected]>, size=446,
class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA, relay=fw.office.sonic.net [209.204.177.119]
Jun 14 21:54:28 b.mail.sonic.net sm-mta[25025]: l5F4sSsY025018: to=<[email protected]>, delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=120446, relay=mailin-02.mx.sonic.net. [209.204.159.4], dsn=2.0.0, stat=Sent (l5F4sS8F011121 Message accepted for delivery)
/sonic-logs/mail/maillog.mxJun 14 21:54:28 b.mx.sonic.net sm-mta[11121]: l5F4sS8F011121: from=<[email protected]>, size=643,
class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA, relay=b.mail.sonic.net [64.142.19.5]
Jun 14 21:54:28 b.mx.sonic.net sm-mta[11129]: l5F4sS8F011121: to=<[email protected]>, delay=00:00:00, xdelay=00:00:00, mailer=esmtp, pri=120643, relay=lds.sonic.net. [208.201.249.231], dsn=2.0.0, stat=Sent (l5F4sSju023934 Message accepted for delivery)
/sonic-logs/mail/maillog.ldsJun 14 21:54:28 eth0.a.lds.sonic.net sm-mta[23934]: l5F4sSju023934: from=<[email protected]>,
size=842, class=0, nrcpts=1, msgid=<[email protected]>, proto=ESMTP, daemon=MTA, relay=b.mx.sonic.net [209.204.159.4]
Jun 14 21:54:30 eth0.a.lds.sonic.net sm-mta[23945]: l5F4sSju023934: to=<[email protected]>, delay=00:00:02, xdelay=00:00:02, mailer=local, pri=31052, dsn=2.0.0, stat=Sent
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Lifecycle of an Email