May be, it's because you use self signed certificate for STARTTLS. I see
no any reason for MSN/Hotmail to check certificate for STARTTLS though,
and anyway it should fallback to unencrypted connection, unless you
published DANE (RFC 7672).

Dave Brockman пишет:
> I'm assisting a client who is having issues receiving from msn/hotmail
> accounts.  The entire rest of the planet can send email to this domain
> without issue, and email *to* MSN/Hotmail is delivered without issue.  I
> am unable to correlate connection attempts with emails sent from hotmail
> web interface.  To date, I have yet to receive an actual (final) NDR
> with any helpful information (But it appears I didn't get the first
> "Delay" NDR for ~12 hours).  There is an encoded text attachment named
> details.txt, I'm not sure what to do with that.  Has anyone experienced
> anything similar?  The domain in question is wdef.com.  Thank you in
> advance for any assistance or thoughts.
>
> Regards,
>
> dtb
>
> Dave Brockman
> Senior Network Engineer
>
>
>
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-- 
Vladimir Dubrovin
@Mail.Ru
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