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send message with O365+OAuth2 hangs indefinitely on Thunderbird 91.11.0 (windows x64)

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I have been successfully using Thunderbird with O365 and OAuth2 since my organization reconfigured for 2FA back in April 2022. Each time I need to reset/change my enterprise e-mail password I must reset my OAuth login, which I did successfully once before by simply deleting saved logins and then re-completing the 2FA process.

After doing that again last week I can no longer send e-mail from TB 91.11.0 -- it successfully connects to smtp.office365.com and then hangs indefinitely on "Sending message...". IMAP is functioning normally (receiving e-mails, moving messages between server folders, etc.). I first confirmed that my (well-documented) my working SMTP settings were not changed.

What I have done to research the issue:

  1. confirmed that security.enterprise_roots.enabled = true (and all org-specific certs are shown) and I have turned up these Iog levels to 'All': mailnews.oauth.loglevel, mailnews.send.loglevel, mailnews.smtp.loglevel
  2. in preferences, confirmed that cookies are accepted from: https://login.microsoftonline.com, https://outlook.office365.com

The error console shows that my TB receives a successful response from the authorization server with a access token (and is refreshing on intervals afterward). When I send a message, the console reports successfully connecting to smtp.office365.com and then simply waits forever without any apparent timeout. When I cancel sending the message, the console reports the socket to the SMTP server is closed. No further detailed information is emitted into the console. I need help with diagnosing the problem further to understand why no progress is made.

I have also tried the following to fix and also re-confirm this issue:

  1. created a full backup of my profile folder
  2. deleted any passwords and/or OAuth2 authentication tokens Thunderbird has remembered for the troubled account
  3. deleted any O365 related cookies
  4. deleted the subject account
  5. restarted Thunderbird
  6. re-created the subject account using manual account setup, and specifically for SMTP: smtp.office365.com:587 with STARTTLS and OAuth2, user name in format 'first.last@domain.gov'.

It was working before. After resetting my password and completing the 2FA process, sending e-mail simply stopped working and I am not sure how to proceed.

Any suggestions for other settings to check as well as how to get TB to emit more detail in the console would be greatly appreciated.

Thanks, Jason

I have been successfully using Thunderbird with O365 and OAuth2 since my organization reconfigured for 2FA back in April 2022. Each time I need to reset/change my enterprise e-mail password I must reset my OAuth login, which I did successfully once before by simply deleting saved logins and then re-completing the 2FA process. After doing that again last week I can no longer send e-mail from TB 91.11.0 -- it successfully connects to smtp.office365.com and then hangs indefinitely on "Sending message...". IMAP is functioning '''normally '''(receiving e-mails, moving messages between server folders, etc.). I first confirmed that my (well-documented) my working SMTP settings were not changed. What I have done to research the issue: # confirmed that security.enterprise_roots.enabled = true (and all org-specific certs are shown) and I have turned up these Iog levels to 'All': mailnews.oauth.loglevel, mailnews.send.loglevel, mailnews.smtp.loglevel # in preferences, confirmed that cookies are accepted from: https://login.microsoftonline.com, https://outlook.office365.com The error console shows that my TB receives a successful response from the authorization server with a access token (and is refreshing on intervals afterward). When I send a message, the console reports successfully connecting to smtp.office365.com and then simply waits forever without any apparent timeout. When I cancel sending the message, the console reports the socket to the SMTP server is closed. No further detailed information is emitted into the console. I need help with diagnosing the problem further to understand why no progress is made. I have also tried the following to fix and also re-confirm this issue: # created a full backup of my profile folder # deleted any passwords and/or OAuth2 authentication tokens Thunderbird has remembered for the troubled account # deleted any O365 related cookies # deleted the subject account # restarted Thunderbird # re-created the subject account using manual account setup, and specifically for SMTP: smtp.office365.com:587 with STARTTLS and OAuth2, user name in format 'first.last@domain.gov'. It was working before. After resetting my password and completing the 2FA process, sending e-mail simply stopped working and I am not sure how to proceed. Any suggestions for other settings to check as well as how to get TB to emit more detail in the console would be greatly appreciated. Thanks, Jason

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