On 13/01/17 17:57, jdehnert wrote:
>>    smtp.office365.com[40.97.0.2]:587:
>>      550 5.7.60 SMTP; Client does not have permissions to send
>>      as this sender
>>
>> which might help explain your problem.
> 
> It might help, but how is it that when I send mail from an account ON the
> relay host, it has no problem connecting and delivering the mail, with the
> exact same user?

user != envelope sender != From: header.  You need to find out what the
envelope sender is, which will be in your logs.

Unfortunately you posted verbose logs, which means that anyone who looks
at them has to weed through 200+ lines of unrelated crap that we don't
need to know.  Turn off verbose logging and log another test message
without it, then we can have a look and tell you more.


Peter

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