Mails not being sent - moved to outbox only

I have two email accounts registered in my K-9 email. For the one, wverything works but not the other one. Mails are not been sent but instead moved to outbox. Sending from outbox doesn´t work and moving it to drafts and sending it from there doesn´t help as it is moved to the outbox once again.

My device is a Lenovo Tab 4 8 Plus Tablet, Android version 8.1.0.

I recorded a log while I tried to send it:

--------- beginning of main
09-08 21:23:10.000  5334  5375 I MessagingController: Running command 'clearNotifications', seq = 92 (foreground priority)
09-08 21:23:10.000  5334  5375 I MessagingController:  Command 'clearNotifications' completed
09-08 21:23:10.027  5334 26206 V LockableDatabase: LockableDatabase: Transaction ended, took 45 ms / com.fsck.k9.storage.messages.SaveMessageOperations.saveMessage(SaveMessageOperations.kt:81)
09-08 21:23:10.057  5334  5375 I MessagingController: Running command 'sendPendingMessages', seq = 93 (background priority)
09-08 21:23:10.071  5334  5375 I MessagingController: Scanning Outbox folder for messages to send
09-08 21:23:10.074  5334  5375 I MessagingController: Send count for message K9LOCAL:a231aa7e-4393-4c88-afb3-fe7a212b6e18 is 0
09-08 21:23:10.111  5334  5375 V LockableDatabase: LockableDatabase: Transaction ended, took 17 ms / com.fsck.k9.mailstore.LocalMessage.setFlag(LocalMessage.java:260)
09-08 21:23:10.112  5334  5375 I MessagingController: Sending message with UID K9LOCAL:a231aa7e-4393-4c88-afb3-fe7a212b6e18
09-08 21:23:10.113  5334  5375 D SmtpTransport: SMTP >>> QUIT
09-08 21:23:10.275  5334 25388 D OpenGLRenderer: endAllActiveAnimators on 0x717277f800 (RippleDrawable) with handle 0x7175243600
09-08 21:23:10.347  5334  5375 V SmtpTransport: SMTP <<< 220 BN0PR04CA0031.outlook.office365.com Microsoft ESMTP MAIL Service ready at Fri, 9 Sep 2022 03:25:03 +0000
09-08 21:23:10.347  5334  5375 D SmtpTransport: SMTP >>> EHLO [IPv6:::1]
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-BN0PR04CA0031.outlook.office365.com Hello [2800:98:1111:6d0:4dc8:ef74:1c45:40b8]
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-SIZE 157286400
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-PIPELINING
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-DSN
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-ENHANCEDSTATUSCODES
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-STARTTLS
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-8BITMIME
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-BINARYMIME
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250-CHUNKING
09-08 21:23:10.413  5334  5375 V SmtpTransport: SMTP <<< 250 SMTPUTF8
09-08 21:23:10.414  5334  5375 D SmtpTransport: SMTP >>> STARTTLS
09-08 21:23:10.482  5334  5375 V SmtpTransport: SMTP <<< 220 2.0.0 SMTP server ready
09-08 21:23:10.655  5334  5375 D SmtpTransport: SMTP >>> EHLO [IPv6:::1]
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-BN0PR04CA0031.outlook.office365.com Hello [2800:98:1111:6d0:4dc8:ef74:1c45:40b8]
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-SIZE 157286400
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-PIPELINING
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-DSN
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-ENHANCEDSTATUSCODES
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-AUTH LOGIN XOAUTH2
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-8BITMIME
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-BINARYMIME
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250-CHUNKING
09-08 21:23:10.723  5334  5375 V SmtpTransport: SMTP <<< 250 SMTPUTF8
09-08 21:23:10.723  5334  5375 D SmtpTransport: SMTP >>> AUTH LOGIN
09-08 21:23:10.789  5334  5375 V SmtpTransport: SMTP <<< 334 VXNlcm5hbWU6
09-08 21:23:10.789  5334  5375 D SmtpTransport: SMTP >>> *sensitive*
09-08 21:23:10.856  5334  5375 V SmtpTransport: SMTP <<< 334 [omitted]
09-08 21:23:10.857  5334  5375 D SmtpTransport: SMTP >>> *sensitive*
09-08 21:23:11.524  5334  5375 V SmtpTransport: SMTP <<< 235 2.7.0 [omitted]
09-08 21:23:11.525  5334  5375 D SmtpTransport: SMTP >>> MAIL FROM:<x@x.com.gt> BODY=8BITMIME
09-08 21:23:11.526  5334  5375 D SmtpTransport: SMTP >>> RCPT TO:<y@y.org>
09-08 21:23:11.601  5334  5375 V SmtpTransport: SMTP <<< 250 2.1.0 Sender OK
09-08 21:23:11.665  5334  5375 V SmtpTransport: SMTP <<< 250 2.1.5 Recipient OK
09-08 21:23:11.666  5334  5375 D SmtpTransport: SMTP >>> DATA
09-08 21:23:11.733  5334  5375 V SmtpTransport: SMTP <<< 354 Start mail input; end with <CRLF>.<CRLF>
09-08 21:23:11.738  5334  5375 D SmtpTransport: SMTP >>> .
09-08 21:23:12.644  5334  5375 V SmtpTransport: SMTP <<< 554 5.2.252 SendAsDenied; x@x.edu.gt not allowed to send as x@x.com.gt; STOREDRV.Submission.Exception:SendAsDeniedException.MapiExceptionSendAsDenied; Failed to process message due to a permanent exception with message [BeginDiagnosticData]Cannot submit message. 0.35250:943E0000, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:3D1D0000, 1.36674:0E000000, 1.61250:00000000, 1.45378:421D0000, 1.44866:2E010000, 16.55847:040F0000, 17.43559:0000000024020000000000000000000000000000, 20.52176:140FD4951200103100000000, 20.50032:140FD4958217000000000000, 0.35180:140FD495, 255.23226:0A000000, 255.27962:0A000000, 255.27962:0E000000, 255.31418:23000000, 0.35250:1F001336, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:22000000, 1.36674:32000000, 1.61250:00000000, 1.45378:27000000, 1.44866:01000000, 16.55847:9D000000, 17.43559:00000000A0030000000000000000000000000000, 20.52176:140FD495120010106A000000, 20.50032:140FD4958217000003003600, 0.35180:6F000000, 255.23226:0A001380, 255.27962:0A000000, 255.27962:32000000, 255.17082:DC040000, 0.27745:0A004200, 4.21921:DC040000, 255.27962:FA000000, 255.1494:0A006400, 0.38698:05000780, 1.41134:46000000, 0.37692:86000000, 0.37948:86000000, 5.33852:00000000534D545000000000, 7.36354:010000000000010958000000, 4.56248:DC040000, 7.40748:010000000000010B4F000100, 7.57132:000000000000000086000000, 4.39640:DC040000, 1.63016:32000000, 8.45434:6E7B493DED3CED47804F30C9BEF2C47A86000000, 1.46798:04000000, 5.10786:0000000031352E32302E353538382E3031383A424E36505231394D42333234393A37326634323531382D396430332D343434612D623464392D6534353233626637656635313A3239383238343A2E4E4554204672616D65776F726B20342E382E393033322E300010A4000000, 7.51330:632B21E41292DA0812000000, 0.39570:12000000, 1.55954:0A000000, 0.49266:02000000, 1.33010:0A000000, 2.54258:00000000, 0.40002:7A000000, 1.56562:00000000, 1.64146:32000000, 1.33010:32000000, 2.54258:DC040000, 255.1750:C1000000, 255.31418:03000336, 0.22753:0300F40F, 255.21817:DC040000, 0.64418:0A002D67, 4.39842:DC040000, 0.41586:CB000000, 4.60547:DC040000, 0.21966:03001610, 4.30158:DC040000[EndDiagnosticData] [Hostname=BN6PR19MB3249.namprd19.prod.outlook.com]
09-08 21:23:12.645  5334  5375 D SmtpTransport: SMTP >>> QUIT
09-08 21:23:12.706  5334  5375 V SmtpTransport: SMTP <<< 221 2.0.0 Service closing transmission channel
09-08 21:23:12.748  5334  5375 E MessagingController: Failed to send message
09-08 21:23:12.748  5334  5375 E MessagingController: com.fsck.k9.mail.transport.smtp.NegativeSmtpReplyException: SendAsDenied; x@x.edu.gt not allowed to send as x@x.com.gt; STOREDRV.Submission.Exception:SendAsDeniedException.MapiExceptionSendAsDenied; Failed to process message due to a permanent exception with message [BeginDiagnosticData]Cannot submit message. 0.35250:943E0000, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:3D1D0000, 1.36674:0E000000, 1.61250:00000000, 1.45378:421D0000, 1.44866:2E010000, 16.55847:040F0000, 17.43559:0000000024020000000000000000000000000000, 20.52176:140FD4951200103100000000, 20.50032:140FD4958217000000000000, 0.35180:140FD495, 255.23226:0A000000, 255.27962:0A000000, 255.27962:0E000000, 255.31418:23000000, 0.35250:1F001336, 1.36674:0A000000, 1.61250:00000000, 1.45378:02000000, 1.44866:22000000, 1.36674:32000000, 1.61250:00000000, 1.45378:27000000, 1.44866:01000000, 16.55847:9D000000, 17.43559:00000000A0030000000000000000000000000000, 20.52176:140FD495120010106A000000, 20.50032:140FD4958217000003003600, 0.35180:6F000000, 255.23226:0A001380, 255.27962:0A000000, 255.27962:32000000, 255.17082:DC040000, 0.27745:0A004200, 4.21921:DC040000, 255.27962:FA000000, 255.1494:0A006400, 0.38698:05000780, 1.41134:46000000, 0.37692:86000000, 0.37948:86000000, 5.33852:00000000534D545000000000, 7.36354:010000000000010958000000, 4.56248:DC040000, 7.40748:010000000000010B4F000100, 7.57132:000000000000000086000000, 4.39640:DC040000, 1.63016:32000000, 8.45434:6E7B493DED3CED47804F30C9BEF2C47A86000000, 1.46798:04000000, 5.10786:0000000031352E32302E353538382E3031383A424E36505231394D42333234393A37326634323531382D396430332D343434612D623464392D6534353233626637656635313A3239383238343A2E4E4554204672616D65776F726B20342E382E393033322E300010A4000000, 7.51330:632B21E41292DA0812000000, 0.39570:12000000, 1.55954:0A000000, 0.49266:02000000, 1.33010:0A000000, 2.54258:00000000, 0.40002:7A000000, 1.56562:00000000, 1.64146:32000000, 1.33010:32000000, 2.54258:DC040000, 255.1750:C1000000, 255.31418:03000336, 0.22753:0300F40F, 255.21817:DC040000, 0.64418:0A002D67, 4.39842:DC040000, 0.41586:CB000000, 4.60547:DC040000, 0.21966:03001610, 4.30158:DC040000[EndDiagnosticData] [Hostname=BN6PR19MB3249.namprd19.prod.outlook.com]
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.mail.transport.smtp.SmtpTransport.buildNegativeSmtpReplyException(SmtpTransport.kt:489)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.mail.transport.smtp.SmtpTransport.executeCommand(SmtpTransport.kt:482)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.mail.transport.smtp.SmtpTransport.executeCommand(SmtpTransport.kt:471)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.mail.transport.smtp.SmtpTransport.sendMessage(SmtpTransport.kt:410)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.backend.imap.ImapBackend.sendMessage(ImapBackend.kt:153)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.controller.MessagingController.sendPendingMessagesSynchronous(MessagingController.java:1573)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.controller.MessagingController$7.run(MessagingController.java:1463)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.controller.MessagingController.runInBackground(MessagingController.java:223)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.controller.MessagingController.access$000(MessagingController.java:109)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at com.fsck.k9.controller.MessagingController$1.run(MessagingController.java:164)
09-08 21:23:12.748  5334  5375 E MessagingController: 	at java.lang.Thread.run(Thread.java:764)
09-08 21:23:12.774  5334  5375 V LockableDatabase: LockableDatabase: Transaction ended, took 22 ms / com.fsck.k9.mailstore.LocalMessage.setFlag(LocalMessage.java:260)
09-08 21:23:12.784  5334  5375 V MessagingController: Skipping sending message K9LOCAL:4c520d7f-3c87-468d-9ead-ad48f823b187
09-08 21:23:12.805  5334  5375 I MessagingController:  Command 'sendPendingMessages' completed
09-08 21:23:18.145  5334  5375 I MessagingController: Running command 'clearNotifications', seq = 94 (foreground priority)
09-08 21:23:18.145  5334  5375 I MessagingController:  Command 'clearNotifications' completed
09-08 21:23:29.000  5334  5375 I MessagingController: Running command 'clearNotifications', seq = 95 (foreground priority)
09-08 21:23:29.000  5334  5375 I MessagingController:  Command 'clearNotifications' completed
09-08 21:24:12.056  5334  5375 I MessagingController: Running command 'clearNotifications', seq = 96 (foreground priority)
09-08 21:24:12.064  5334  5375 I MessagingController:  Command 'clearNotifications' completed
09-08 21:24:14.746  5334 25388 D OpenGLRenderer: endAllActiveAnimators on 0x7175191800 (ConstraintLayout) with handle 0x71728a6f80
09-08 21:24:16.146  5334 25388 D OpenGLRenderer: endAllActiveAnimators on 0x716cff5c00 (FrameLayout) with handle 0x71752755c0
09-08 21:24:23.815  5334 25388 D OpenGLRenderer: endAllActiveAnimators on 0x716cea5800 (MenuPopupWindow$MenuDropDownListView) with handle 0x71728a69a0
09-08 21:24:29.512  5334 26311 V LogcatLogFileWriter: Writing logcat output to content URI: content://com.android.providers.downloads.documents/document/1324

From the errors, this one stands out:

09-08 21:23:12.644 5334 5375 V SmtpTransport: SMTP <<< 554 5.2.252 SendAsDenied; x@x.edu.gt not allowed to send as x@x.com.gt

Your address and/or sending email address for the SMTP server may not be correct.

2 Likes
not allowed to send as x@x.com.gt

The x@x.edu.gt is my actual email address which works for other mail clients.
The server settings are identical with the ones in Thunderbird on my PC.
I have nowhere set that an email sent should be redirected to a “.com.gt” domain.

Not sure where this is set. My approach would be to export the settings for this account. Then you can search for

x@x.com.gt

on that file which might give you an idea where it was set.

Maybe it is set on the identity? Settings → account → sending mail → manage identities

2 Likes

That I tried but I did not run into that issue. But either I did not hit the correct setting or it is depending on server config as well.

The identity was the issue. I had mistakenly written there .com.gt instead of .edu.gt.
Don’t know why the identity is being mixed with the server settings but anyhow thank you very much for your help.

3 Likes

Thanks for the fix.I had the same issue with a Gmail account, which had been working up until mid-September 2022.

K9 developers, please separate Identity from login credentials. They are two separate concepts. The sender address is picked up from Identity. Users need the option for it to be different from the username used for login credentials.

Umm… They ARE separated. I use version 6.202 and see this:

  • The identity is defined in Settings → account → sending mail → manage identities. (You may have more than one identity.)
  • The credentials for sending mail is defined in Settings → account → sending mail → Outgoing mail. (You can have only one set of credentials.)

Please describe in more details what you think is wrong. (Or tell me how I misunderstood what you meant…)

Thanks for the response. Running 6.202, Gmail won’t accept a send request unless the email address set in Identity matches the email address in the user credentials for the outgoing mail server. This is new behavior, started within the last few days.

Using standard password authentication. This is not a Google workspace account, so password authentication is still accepted.

1 Like

I am running 6.30x (Beta) - and I tested to create an alternative identity with mail adress using different domain.

It worked - I could always send using my mail provider.
The only difference was if it could be received or not:

  • worked for Adresses on my mail provider and on proton mail.
  • did NOT receice any mail on GMX and web.de - no bounce and not in spam. Just swallowed.

So I guess in general K9 works fine. It seems to be a security setting from your mail provider - maybe enabled a few days ago

Reinstalling 6.202 resolved the issue. With different email addresses for Identity and username for the outgoing SMTP server, I can again send emails.

1 Like