Re: Authentication unsuccessful relaying from Postfix to Microsoft ESMTP MAIL Service
On Sun, 9 May 2010 17:06:52 +0100
Clive Standbridge <Clive.Standbridge@myriadgroup.com> wrote:
> Hi,
>
> I'm trying in vain to relay external mail from postfix on a Debian
> lenny machine to a Microsoft SMTP server on the Internet. I've been
> reading and searching for days. I've tried numerous combinations of
> settings although I'm note certain what they all do and am
> experiencing information overload.
>
> I am trying to migrate from one MS server to another.
> OLDSERVER runs on port 25.
> NEWSERVER runs on port 587. Supposedly it requires TLS but I'm not
> certain of that (more later).
I don't have a solution, just one possibly helpful bit of advice: swaks
is the tool for troubleshooting this sort of thing. You have gotten
lots of useful information from Postfix and telnet, but I'd try using
swaks to communicate with the server with and without TLS, and you'll
see, for any combination of connection and authentication options
that you try, what works and what errors are received on failure.
Celejar
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