On Wed, Oct 20, 2021 at 10:03:10PM +0200, Damian wrote:

> > Oct 20 20:09:37 libertyfp postfix/smtpd[174449]: warning:
> > unknown[87.246.7.245]: SASL LOGIN authentication failed: UGFzc3dvcmQ6
> > Oct 20 20:09:37 libertyfp postfix/smtpd[174449]: disconnect from
> > unknown[87.246.7.245] ehlo=1 auth=0/1 rset=1 quit=1 commands=3/4
> 
> Shouldn't there be a starttls as part of the command statistics?
> Because without VPN, there is. Maybe your VPN provider is messing with
> outgoing smtp?

Well spotted, for once I'm the one showing insufficient attention to
detail.  The reported working connection had:

    Oct 20 21:17:00 libertyfp postfix/smtpd[175562]:
    disconnect from 87.sub-174-212-171.myvzw.com[174.212.171.87]
    ehlo=2 starttls=1 auth=1 mail=1 rcpt=1 data=1 quit=1 commands=8

And the reason that Postfix then fails at the SASL stage may be that
Postfix by default does not offer plaintext SASL mechanism when TLS
is not used.

So, if the VPN strips STARTTLS, that could explain the symptoms.

-- 
    Viktor.

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