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Exchange Hybrid environment mail flow issue

Posted on 2016-07-18
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Last Modified: 2016-07-26
So here is the scenario:

- network with the following components: sonicwall NSA firewall, sonicwall email appliance
- on-premise Exchange 2013 server
- Office 365 account
- hybrid configuration wizard run successfully
- azure AD sync installed

We currently have the following mail flow conditions:
- MX records point to on-premise Exchange server
- mail flows to and from external email addresses from on-premise or O365 mailboxes
- mail flows from on-premise Exchange mailboxes to O365 mailboxes
- mail does NOT flow from O365 mailboxes to on-premise mailboxes

I can say that I have not updated the TXT records with the updated federation information (is that supposed to be internal and external DNS records?) but I am not sure if that is related.

Can anyone assist with troubleshooting this issue? I am not sure where to start.
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Question by:twinstatevdv
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Author Comment

by:twinstatevdv
ID: 41718096
Also, all inbound email traffic on port 25 is routed through the sonicwall email appliance.
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Expert Comment

by:Jian An Lim
ID: 41721004
Rerun hybrid configuration wizard again

On Office 365, check it's outbound connector.
depends on version, you should have one outbound connector

try to test connectivity on that

you can run get-outboundconnector | fl and paste the result here
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Accepted Solution

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Jian An Lim earned 500 total points
ID: 41721014
one thing, email from Office 365 back to On-premise should not pass through sonic wall.
It must arrive directly
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Author Comment

by:twinstatevdv
ID: 41721076
What IP addresses and ports should I forward at the firewall direct to the exchange server? I know there is a set of EOP addresses.
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Expert Comment

by:Jian An Lim
ID: 41721519
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Author Comment

by:twinstatevdv
ID: 41727609
THanks for the info! Which ports should I be forwarding?
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Expert Comment

by:Jian An Lim
ID: 41728613
port 25 for sMTP
port 443 for EWS and HTTPS
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Author Comment

by:twinstatevdv
ID: 41729446
got it, I will try that with the EOP addresses; my only concern is that we might be allowing non-hybrid email messages from Office 365 sources to bypass the email appliance.
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Expert Comment

by:Jian An Lim
ID: 41729680
non-hybrid email message?
the connector should only bring back any email that is mail user, nothing else.

also, you might want to upgrade your azure AD sync to AADConnect as the previous version have been deprecated.
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Author Closing Comment

by:twinstatevdv
ID: 41730099
Thank you for the assistance! Email appears to be flowing as desired.  :)
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