On Feb 20, 2016, at 4:34 PM, Adrian Neale (iComms)
Hi there, just joined to try and get some knowledge/help on an issue when
getting emails delivered from (particularly) Hotmail/Outlook.com but
occasionally Gmail addresses. I consulted RFC5321 and it does say the mail
delivery will be tried in order of MX preference.
You'll likely find more help with operational problems on the mailop list -
it's much more about ops and less about developing SMTP related protocols.
There are all sorts of problems you could have with your setup; it's more
likely that someone there will be able to help if you share the domains and IP
addresses involved, and any bounce or deferral messages or logs.
We have set up a Sophos UTM which is a pretty sophisticated device. This is
in front of an Exchange server and filters all incoming/outgoing emails.
The domain being used is, say, abc.com
Our MX records for this domain are:
The 3rd priority MX record is in the event of an outage, the emails queue and
return to the top MX entry once the mail server returns from e.g. a reboot or
Internet downtime. It is hosted in a different country to the top priority
What we are finding is that 90% of Hotmail/Outlook.com emails sent to the
domain abc.com are coming from mxbackup.3rdparty.com. All other domains
behave as expected and come in via 0 autodiscover.abc.com. Some Gmails
follow this behaviour too.
This is where the IETF comes in as it would appear to go against the RFC for
What brought this to our attention was that our Sophos UTM instantly started
rejecting emails from our 3rd party MX provider, all of them from
It is happening with all 3 of the UTM devices that we have fitted so far, all
on different domains, different public IP addresses, all in Gibraltar. Our
3rd Party MX is located in Manchester, United Kingdom.
We have obviously now added our 3rd Party as an upstream relay but this is
not ideal – why are these emails going to the 3rd priority MX record in the
The primary MX public IP addresses on all 3 UTM's are not blacklisted and
pretty much have 99% or higher availability.
I am going to be asking Sophos if the UTM is in any way delaying it’s
response to the Microsoft mail servers to eliminate it being the UTM taking
too long to reply for Hotmail’s/Gmail’s liking.
I do not think that is the case as it is only with these two email providers
that we have the issue.
Thanks in advance for any possible help or advice.
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