James B. Byrne: [ Charset ISO-8859-1 converted... ] > > > 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