Outlook on Android, Dovecot, Postfix

Have a look at this chain as it's similar to what you have

I am going to assume your domain is: mail.ve3nrt.net as per your previous post

A) A gentle review of Port Numbers and how they should work

B) I can see you have port 587 and 993 open which are SMTP over SSL and IMAP over SSL

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C) You should review the concept of STARTTLS as it will explain your observations below

Outlook Windows works when I use TLS on port 143, or SSL on 993, although 993 doesn’t work with TLS. I even got RPA (require password authentication) to work for the first time ever. By default, Outlook for Android tries to use 993, I found out, but forcing it to 143 by specifying the port after the fqdn of the imap server doesn’t work either, although the port it tries to connect on does indeed change

Your observations are what I would expect to see from a mail server. My testing is below

SMTP on Port 25: No SSL Handshake with No starttls

SMTP on Port 25 with STARTTLS: Handshake

IMAP on Port 143: No SSL Handshake with no STARTTLS

IMAP on Port 143: SSL Handshake with STARTTLS

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SMTPS on port 587 - Handshake with STARTTLS

SMTPS on port 587 - No Handshake with no STARTTLS

IMAPS on Port 993 - handshake with no STARTTLS flag

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