Re: Re: Authentication unsuccessful relaying from Postfix to Microsoft ESMTP MAIL Service

[Clive Standbridge <Clive.Standbridge@myriadgroup.com>]

> The problem with postfix is that it runs chrooted and the CA
> certificates are not copied into the chroot.  See #287795¹.
> 
> Sven
> 
> ¹ http://bugs.debian.org/cgi-bin/bugreport.cgi?bug=287795

Hi Sven,

Thanks for that suggestion. I had seen that bug and discounted it
because the patch is only effective if smtp_tls_CApath is set, and
mine wasn't set. But your mail prompted another look, and with both
smtp_tls_CApath = /etc/ssl/certs and applying the patch from #287795,
it banished the "certificate verification failed" and changed
"Untrusted TLS connection established" to "Trusted TLS connection
established".

So that's progress :-)

Unfortunately it's still failing to authenticate. From mail.log:
May  9 21:49:18 rimmer postfix/smtp[8121]: 5DE243A66: to=<MY-EMAIL-ADDRESS>, relay=NEWSERVER[NEWSERVER-IPADDR]:587, delay=5.5, delays=0.02/0.03/5.4/0, dsn=4.7.3, status=deferred (SASL authentication failed; server NEWSERVER[NEWSERVER-IPADDR] said: 535 5.7.3 Authentication unsuccessful)

Thanks,
Clive