Hello,
I may be mistaken, but I don't see "auth_mechanism = plain login" in your
configuration. It's possible that you are using something different for
authentication, but I don't see it in the configuration.

On Wed, May 17, 2023 at 4:04 PM Ralf Becker via dovecot <dovecot@dovecot.org>
wrote:

> Dovecot 2.3.20 including it's submission server works well with all
> sorts of clients, but Outlook.
>
> Outlook works / can connect to Dovecot IMAP service with same
> certificate TLS config, but it fails to connect using SMTPs on port 465.
> Other clients connect and send mails without problem, also openssl
> s_client can connect and reports no problems.
>
> I tried with Outlook Version 365 on Windows 11 (no cloud) and
> "Microsoft® Outlook® 2021 MSO (Version 2304 Build 16.0.16327.20200)
> 64-bit".
>
> I already enabled all submission_client_workarounds and lowered
> min_ssl_version from TLSv1.2 to TLSv1, but that changed nothing.
>
> I can see nothing failing in the logs, thought the OL connection wizard
> always check IMAP and SMTP together, so it's hard to say what the
> problem is.
>
> The same two Outlook version connect without a problem to Postfix
> authenticating via SASL to Dovecot also requiring a minimum TLS version
> of 1.2.
> They just wont connect with Dovecot submission server.
>
> Any ideas what's wrong, or how to debug that further?
>
> Ralf
>
> --
>
> Ralf Becker
> EGroupware GmbH [www.egroupware.org]
> Handelsregister HRB Kaiserslautern 3587
> Geschäftsführer Birgit und Ralf Becker
> Leibnizstr. 17, 67663 Kaiserslautern, Germany
> Telefon +49 631 31657-0
> _______________________________________________
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>


-- 
Andrzej
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