1 Topic by epg_will

  • epg_will
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Topic: Outlook keeps asking for my email credentials

==== REQUIRED BASIC INFO OF YOUR IREDMAIL SERVER ====
- iRedMail version (check /etc/iredmail-release): 0.9.7
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====

Outlook is forcing us to reenter our credentials multiple times (if that even works) in order to send emails. The issue started yesterday (9/7). The web portal doesn't have a problem.

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2 Reply by ZhangHuangbin

  • ZhangHuangbin
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Re: Outlook keeps asking for my email credentials

Any related error in dovecot log files? /var/log/dovecot/*.log.

3 Reply by epg_will (edited by epg_will 2021-09-09 20:41:46)

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Re: Outlook keeps asking for my email credentials

From dovecot-imap.log

I am seeing authentication failures, and the time is off by over 5 minutes.

4 Reply by epg_will

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Re: Outlook keeps asking for my email credentials

My attempt to send a test email would not show up in the dovecot-imap.log until the pop up prompting for my email credentials went away.

5 Reply by ZhangHuangbin

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Re: Outlook keeps asking for my email credentials

Do you use self-signed ssl cert or a valid one?

6 Reply by epg_will

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Re: Outlook keeps asking for my email credentials

It's from DigiCert. Fixing the time sync appears to have fixed the worst of the issues. It's still popping up occasionally, but it's now happening less and less.