James B. Byrne:
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> 
> 
> On Tue, December 22, 2020 13:27, Viktor Dukhovni wrote:
> 
> >
> > Your suspicions are unfounded.  The client is rejecting the server's
> > certificate chain with a fatal certificate unknown alert.  That's the
> > issue to fix.  All else is distraction.
> >
> 
> After reviewing Postix logs with smtpd_tls_logging turned up to 3
> I arrived at the same conclusion a little while ago.  I am just
> bereft of ideas as to how to proceed at the moment.

Here is a suggestion:

- You see a different behaviors with the Javamail app on port 25
and some other Java tool on port 465. One rejects the server
certficate, while other does not.

- The Postfix services on port 465 and 25 use the same TLS settings
(apart from tls_wrappermode which is enabled on port 465).

- The difference must then be on the client side, in the way that
the client verifies the server cerificate.

Therefore I suggest that you move your attention to the client side.

        Wietse

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