> We have witnessed the same issue on one of our mailservers. Both
> servers are the same (postfix/debian), with the same config, both have
> letsencrypt certificates.

I'm just curious, which openssl version are you using?

> However we got customer complaints only for 1 server. Renewing the
> cert did not help, but trying the cert from the other server helped
> (of course showing warning about wrong domain) and affected clients
> were again able to connect using TLS.

Educating customers to ignore this kind of warning is not a good idea.
Try to disable session tickets for submission instead:

(in master.cf)

# ==========================================================================
# service type  private unpriv  chroot  wakeup  maxproc command + args
#               (yes)   (yes)   (yes)   (never) (100)
# ==========================================================================
...

submission inet n       -       n       -       -       smtpd
 ...
 -o tls_ssl_options=NO_TICKET

Add this option to submission and smtps (if configured) and restart postfix.


> Any idea why it works with the other cert? I can provide privately
> postfix host/port for both working and non-working certs. Tcpdump
> maybe only tomorrow/Monday as I don't have direct access to any
> affected Windows/Outlook machine.
> 
> Can I safely turn off smtpd_tls_always_issue_session_ids as mentioned
> earlier? It won't have any negative impact (except performance)?

Try my suggestion above, then there is no need to set
smtpd_tls_always_issue_session_ids. Session tickets are a kind of
cache to speed up subsequent tls connections, so it's not a security
problem when it's disabled.

Best regards
Gerald

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