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If I connect outlook to port 465 with the same details, but for the mailbox, if I use IMAP, it won't send. If I use POP3 for the mailbox, it is able to send. And, I have postfix and dovecot installed in my mail server. What could possibly causing this? If I use thunderbird, it works. But not with Outlook when using IMAP for the mailbox. I am confused how sending mail is related to IMAP... I usually connect IMAP with port 993, and SSL is configured correctly, and I connect POP3 with 995.

The thing is, that everything goes well with IMAP. But it just doesn't seem to care about connecting to SMTP. Everything was fine until I changed my dovecot auth to use MySQL database instead of /etc/passwd.

EDIT:

I realized that Outlook doesn't even try to authenticate to the SMTPS server. Even if I enter the wrong password, Outlook just continues, no errors, and no access info in the logs. So, I think this must be a outlook problem. But I am still not so sure. I could create a test account, if anyone is able to test it, and see if they can reproduce the issue.

Another update:

I just saw that, even if I use the IP instead of the domain. It still won't work. And I am aware that many bots are trying to make unauthorized connection attempts to my SMTP server. Doesn't seem good right? So, I wish to hide some of my conf in these questions. Ask me, and I will post the conf. But please ask the particular conf which is needed.

  • @tater, okay now. Sorry about that. I delete them because I fix the issue myself. Maybe from next time, I should answer it here. And I still get downvotes, and it hurts. Let me undelete all of them. Sure –  Dec 19 '20 at 14:30
  • Go have a look at all of my questions. I have undeleted them :) They won't be deleted any soon. Thats for sure –  Dec 19 '20 at 14:33
  • You should first learn how to ask good questions with enough details for anyone else than you to even try and answer them. – Esa Jokinen Dec 19 '20 at 15:19
  • @EsaJokinen I know how. But I am in an urgent situation. Sometimes, I am too lazy to give all the info. –  Dec 19 '20 at 16:48

1 Answers1

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Depending on the client, sending mail might fail for example if IMAP fails to save a copy to the Sent folder. This part has nothing do with SMTP, as SMTP isn't typically used for sending copies to oneself (and if it was, they would probably appear in Inbox). Some clients may also send first and save afterwards, so you may even end up sending mail without knowing it was delivered.

Esa Jokinen
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  • it actually goes into the sent folder. But it says it is sent. But it does not even connect to the SMTP server. I will reinstall dovecot –  Dec 19 '20 at 16:50
  • The thing is, that everything goes well with IMAP. But it just doesn't seem to care about connecting to SMTP. Everything was fine until I changed my dovecot auth to use MySQL database instead of /etc/passwd. –  Dec 20 '20 at 04:27
  • This is exactly the like of information you should put on your question... – Esa Jokinen Dec 20 '20 at 05:03
  • still missing required informations, did you tried thunderbird as a work around? – djdomi Jan 02 '21 at 08:42
  • @djdomi, yeah thunderbird works. But, there is no thunderbird for android or iOS... So... –  Jan 03 '21 at 06:43
  • I have to give the bounty to someone instead of it going to waste, so... It expires in 50 mins, so –  Jan 03 '21 at 06:46
  • on Android look for k9 Mail, Aquamail or similar and i belive that this exists aldo for ios – djdomi Jan 03 '21 at 12:49