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Delivery is delayed to these recipients or groups: office365

Posted on 2015-01-20
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Last Modified: 2015-01-20
New SBS 2011 installation is having trouble sending to Office 365 accounts.


Delivery is delayed to these recipients or groups:
user@domain.com
Subject: Test
This message hasn't been delivered yet. Delivery will continue to be attempted.
The server will keep trying to deliver this message for the next 1 days, 19 hours and 54 minutes. You'll be notified if the message can't be delivered by that time.

I know that at least 2 of these domains that bounce back are on Office365. I suspect that maybe more of them are as well.

I forgot to setup reverse DNS when I deployed, but that was rectified 5-6 days ago.

MXToolbox says that we're good other than a long transaction time. Not sure what's up with that. When I click for more information it doesn't give me much:

We were able to connect to your mail server on port 25, but the diagnostic session took longer than expected. This could indicate that your email server is under heavy load.
Here are the levels for which we issue warnings and alerts:

Over 5 Seconds: Warning
Over 8 Seconds: Alert
Having this warning on your lookup does not necessarily mean that you will have a problem receiving mail. It is simply a warning that things are less than optimal. This could end up causing users to experience delays with inbound mail.
C---LOE---MXtoolbox.GIF
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Question by:MJCS
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David Atkin earned 500 total points
ID: 40559905
Hello,

Do you have your DNS on the server configured for root hints (is by  default)?  This can be a common cause.  Switch to DNS Forwarders if you haven't already.
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by:MJCS
ID: 40559909
would that affect inbound e-mail?
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Expert Comment

by:David Atkin
ID: 40559926
No, it would only affect outbound.

Don't be too concerned over the transaction times - If you do the same test on an Office 365 server you will get something similar.
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by:MJCS
ID: 40559933
would it make sense that it would delay sending to only office365 domains?
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Expert Comment

by:David Atkin
ID: 40560027
It may be doing it with other domains as well.  Check your queues.  Exchange Management Console> ToolBox

Its a good place to start.
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