SMTP not working on .edu Outlook/Exchange/Office365 email

[Starcr0ss]

Checklist

• I have used the search function to see if someone else has already submitted the same bug report.
• I will describe the problem with as much detail as possible.

App

Thunderbird for Android

App version

13.0

Where did you get the app from?

F-Droid

Android version

Android 16, LineageOS 23.0

Device model

Sony Xperia 1 II, XQ-AT52

Steps to reproduce

1. Log into my university's Outlook email using OAuth 2.0
2. Accept recommended config (same results when using new config here
3. Successfully logs into IMAP
4. Fails to log into SMTP Outgoing Server

Expected behavior

Thunderbird should seamlessly log into the SMTP server in the same way it does for the IMAP server.

Actual behavior

The app fails to authenticate for just the SMTP outgoing server. See screenshot.

Note: I am able to log in and send emails perfectly fine on FairEmail.
Note 2: This issue does not occur with my personal "@outlook.com" email on Thunderbird.

Logs

k9mail-logs.txt

[platform34]

Your issue sounds like a duplicate of #9160 and fixed by PR #9823
The fix is assigned to Thunderbird 14's milestone.

You can try Thunderbird beta 14.3 and feedback if is works successfully
https://github.com/thunderbird/thunderbird-android/releases

[Starcr0ss]

Your issue sounds like a duplicate of #9160 and fixed by PR #9823 The fix is assigned to Thunderbird 14's milestone.

You can try Thunderbird beta 14.3 and feedback if is works successfully https://github.com/thunderbird/thunderbird-android/releases

New issue this time around. It doesn't explicitly error out, but it does just stay on this screen endlessly on v14 Beta 3
See:

[Starcr0ss]

Oh wait. It finally errored out, different error.

[platform34]

Hi StarCr0ss

The log from your initial post shows shows 2 distinct issues which were the same ones observed in #9160

1. Failure Fetching Autoconfig

Your log shows DNS resolution issues, possibly IP v6 related. Can you investigate this.
Are you connecting over a VPN?

- Error fetching Autoconfig from URL: http://redacted-mail-server.edu/.well-known/autoconfig/mail/config-v1.1.xml
- java.net.SocketTimeoutException: failed to connect to redacted-mail-server.edu/172.23.82.102 (port 80) from /10.111.126.31 (port 48008)
- at java.net.Inet6AddressImpl.lookupHostByName(Inet6AddressImpl.java:156)

- Failed to get MX record for domain: redacted-mail-server.edu
- org.minidns.util.MultipleIoException: Poll timed out, failed to connect to /8.8.8.8 (port 53) from /10.111.126.31 (port 39572)

2. XOAuth2 SMTP Authentication Failure

Your log shows ...

- saslOAuth: failed to authenticate.
- com.fsck.k9.mail.transport.smtp.NegativeSmtpReplyException: Authentication unsuccessful
- com.fsck.k9.mail.AuthenticationFailedException: AUTH XOAUTH2 failed
- at com.fsck.k9.mail.transport.smtp.SmtpTransport.handlePermanentOAuthFailure(SmtpTransport.kt:580)

Could you attach a debug log from beta 14.3?

In the other ticket, @rafaeltonholo created a debug build. Perhaps trying this will reveal greater detail in it's debug log.