On Tue, Dec 22, 2020 at 02:00:27AM +0100, Jaroslaw Rafa wrote:

> If you are able to connect via 465, then maybe the application just isn't
> designed to use "inline" TLS, but rather uses only SMTP-over-TLS? The latter
> is supported on port 465, while submission via port 587 requires first
> plaintext connection and then dynamic in-session switchover to TLS, using
> STARTTLS command. Maybe your application just does not support that?

It clearly supports STARTTLS, since it is actually performing the TLS
handshake, and abandons it after receiving certificates it is not happy
with.

-- 
    Viktor.

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