> On Sep 21, 2016, at 6:19 AM, Gilles Chehade via mailop <mailop@mailop.org> 
> wrote:
> On Wed, Sep 21, 2016 at 05:49:48AM -0700, Steve Atkins wrote:
>>> On Sep 21, 2016, at 4:02 AM, Gilles Chehade <gil...@poolp.org> wrote:
>>> I'm wondering if there is something wrong in the format of our headers
>>> and if this could affect users of our software disregarding the kind
>>> of mails they send with it. I've been tackling this for hours before
>>> contacting the mailing list.
>>> Any help would be greatly appreciated, I'm running out of ideas :-)
>> Sharing a sample of those headers on a paste site (and maybe
>> a protocol level trace of a failing transaction) might get you some
>> feedback on whether anything looks off about them.
> Hi,
> The following paste is a trace from the mta engine starting right after
> STARTTLS is established:
>    http://pastebin.com/VY8zxcjQ
> The following paste is a complete copy paste of the raw message as seen
> in the Junk folder:
>    http://pastebin.com/uTyx90dE

Nothing stands out as being problematic in any of that. I'd guess it's
not MTA-specific, rather something about the reputation (or lack thereof)
of your smarthost from Microsoft's perspective, something content-related,
or just MS being inscrutable.

... uh, given you're doing MTA development, you don't have test autoresponders
or anything else that might backscatter on that box, do you?

> As I said earlier, I'm not necessarily looking to troubleshoot this one
> particular message / domain, just trying to make sure that there is not
> something in the MTA generated headers that makes microsoft unhappy, we
> have been unable to find a single user that can inbox the most simple
> mail at microsoft which worries me.
> As a side note, two postfix users also went Junk by default so if I
> can just rule out it's something bad that we, opensmtpd, do, I'll be
> plenty happy ;-)


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