The reason that this bug is critical is because a user does not know an
email was not sent. The solution that is needed is for the user to know
that it has not been sent.  A workaround does not help if a user does
not know there is a problem. I raised the issue many years ago and have
kept an eye that the brief message that sending fails, before the email
is put in the sent folder, does not appear.  For me the circumstances
that originally caused it seem no longer to apply.

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https://bugs.launchpad.net/bugs/1215882

Title:
  Emails are silently discarded on 554 reply to STARTTLS

Status in Mozilla Thunderbird:
  Confirmed
Status in thunderbird package in Ubuntu:
  Triaged

Bug description:
  It seems that emails are silently discarded when the remote SMTP
  server replies with an error on STARTTLS. Here is an example smtp log
  created with NSPR_LOG_MODULES='smtp:5,timestamp':

  2013-08-23 11:10:25.548708 UTC - 43480896[7fe10164b370]: SMTP Connecting to: 
mail.trialphaenergy.com
  2013-08-23 11:10:26.513993 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:26.514026 UTC - 43480896[7fe10164b370]: SMTP Response: 220 
mail.trialphaenergy.com Microsoft ESMTP MAIL Service ready at Fri, 23 Aug 2013 
04:10:25 -0700
  2013-08-23 11:10:26.514047 UTC - 43480896[7fe10164b370]: SMTP entering state: 
14
  2013-08-23 11:10:26.514069 UTC - 43480896[7fe10164b370]: SMTP Send: EHLO 
[10.11.206.9]
  2013-08-23 11:10:27.144751 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144791 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-mail.trialphaenergy.com Hello [10.11.10.19]
  2013-08-23 11:10:27.144808 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144817 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-SIZE
  2013-08-23 11:10:27.144828 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144839 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-PIPELINING
  2013-08-23 11:10:27.144846 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144851 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-DSN
  2013-08-23 11:10:27.144857 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144862 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-ENHANCEDSTATUSCODES
  2013-08-23 11:10:27.144868 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144885 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-STARTTLS
  2013-08-23 11:10:27.144889 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144893 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-AUTH NTLM
  2013-08-23 11:10:27.144897 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144900 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-8BITMIME
  2013-08-23 11:10:27.144904 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144920 UTC - 43480896[7fe10164b370]: SMTP Response: 
250-BINARYMIME
  2013-08-23 11:10:27.144926 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.144931 UTC - 43480896[7fe10164b370]: SMTP Response: 250 
CHUNKING
  2013-08-23 11:10:27.144936 UTC - 43480896[7fe10164b370]: SMTP entering state: 
4
  2013-08-23 11:10:27.144961 UTC - 43480896[7fe10164b370]: SMTP entering state: 
21
  2013-08-23 11:10:27.144968 UTC - 43480896[7fe10164b370]: SMTP Send: STARTTLS
  2013-08-23 11:10:27.757848 UTC - 43480896[7fe10164b370]: SMTP entering state: 0
  2013-08-23 11:10:27.757881 UTC - 43480896[7fe10164b370]: SMTP Response: 554 
Policy violation. Email Session ID: {521742ED-1-F0B0B0A-FFFF}
  2013-08-23 11:10:27.757893 UTC - 43480896[7fe10164b370]: SMTP entering state: 
19
  2013-08-23 11:10:27.757900 UTC - 43480896[7fe10164b370]: SMTP entering state: 
21
  2013-08-23 11:10:27.757905 UTC - 43480896[7fe10164b370]: SMTP Send: QUIT
  2013-08-23 11:10:27.757915 UTC - 43480896[7fe10164b370]: SMTP entering state: 0

  
  The UI, however, gives no indication of failure and closes the compose window 
after the apparent successful submission to the smtp server.

  
  If the user has not configured a Sent folder this results in data loss. Even 
if the user has configured a sent folder, he receives no indication that the 
email has not been sent.

  ProblemType: Bug
  DistroRelease: Ubuntu 13.04
  Package: thunderbird 17.0.8+build1-0ubuntu0.13.04.1
  ProcVersionSignature: Ubuntu 3.8.0-27.40-generic 3.8.13.4
  Uname: Linux 3.8.0-27-generic x86_64
  AddonCompatCheckDisabled: False
  ApportVersion: 2.9.2-0ubuntu8.3
  Architecture: amd64
  AudioDevicesInUse:
   USER        PID ACCESS COMMAND
   /dev/snd/controlC0:  nikratio   2425 F.... pulseaudio
  BuildID: 20130803220711
  Channel: Unavailable
  Date: Fri Aug 23 13:05:30 2013
  ForcedLayersAccel: False
  IfupdownConfig:
   # interfaces(5) file used by ifup(8) and ifdown(8)
   auto lo
   iface lo inet loopback
  InstallationDate: Installed on 2013-07-30 (23 days ago)
  InstallationMedia: Ubuntu 13.04 "Raring Ringtail" - Release amd64 (20130424)
  MarkForUpload: True
  PrefSources:
   prefs.js
   
/usr/lib/mozilla/extensions/{3550f703-e582-4d05-9a08-453d09bdfdc6}/{847b3a00-7ab1-11d4-8f02-006008948af5}/defaults/preferences/enigmail.js
   
/usr/lib/mozilla/extensions/{3550f703-e582-4d05-9a08-453d09bdfdc6}/{847b3a00-7ab1-11d4-8f02-006008948af5}/defaults/preferences/000system.js
  Prefs:
   extensions.lastAppVersion: "17.0.8" (prefs.js)
   network.cookie.prefsMigrated: true (prefs.js)
   places.database.lastMaintenance: 1377252192 (prefs.js)
   places.history.expiration.transient_current_max_pages: 104858 (prefs.js)
   privacy.donottrackheader.enabled: true (prefs.js)
  ProcEnviron:
   TERM=xterm
   PATH=(custom, no user)
   XDG_RUNTIME_DIR=<set>
   LANG=en_US.UTF-8
   SHELL=/bin/bash
  Profiles: Profile0 (Default) - LastVersion=17.0.8/20130803220711
  RelatedPackageVersions:
   icedtea-7-plugin  1.3.2-1ubuntu1.1
   totem-mozilla     3.6.3-0ubuntu6
   rhythmbox-mozilla 2.98-0ubuntu5
  RunningIncompatibleAddons: False
  SourcePackage: thunderbird
  UpgradeStatus: No upgrade log present (probably fresh install)
  dmi.bios.date: 02/04/2013
  dmi.bios.vendor: LENOVO
  dmi.bios.version: G6ET93WW (2.53 )
  dmi.board.asset.tag: Not Available
  dmi.board.name: 3444F8U
  dmi.board.vendor: LENOVO
  dmi.board.version: Win8 Pro DPK TPG
  dmi.chassis.asset.tag: No Asset Information
  dmi.chassis.type: 10
  dmi.chassis.vendor: LENOVO
  dmi.chassis.version: Not Available
  dmi.modalias: 
dmi:bvnLENOVO:bvrG6ET93WW(2.53):bd02/04/2013:svnLENOVO:pn3444F8U:pvrThinkPadX1Carbon:rvnLENOVO:rn3444F8U:rvrWin8ProDPKTPG:cvnLENOVO:ct10:cvrNotAvailable:
  dmi.product.name: 3444F8U
  dmi.product.version: ThinkPad X1 Carbon
  dmi.sys.vendor: LENOVO

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