On Mon, Sep 14, 2020 at 07:01:25PM -0700, Marc MERLIN via Exim-users wrote:
> I'm more confused though, because with Mail -v, starttls does not
> happen, or looks like it doesn't, but maybe does and it's not shown
> in the newer exim.

 With traffic analyzer you can get direct answer is there STARTTLS or no.

> Either way, the debian10 Email isn't going through.
> 
> Ok, so now I'm comparing the rest of the d+all that works (9) vs the one that 
> doesn't (10)

 Probably your configurations (deb9 vs deb10) are different. Compare files
 /var/lib/exim4/config.autogenerated (or even /etc/exim4/conf.d/ trees).
 Check carefully debian parameters AUTH_CLIENT_ALLOW_NOTLS_PASSWORDS.
-- 
 Eugene Berdnikov

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