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Exchange 2010 External Email Not Working

Posted on 2012-03-17
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Last Modified: 2012-03-23
Hi All.

I have recently completed a migration from SBS 2008 Standard to SBS 2011 Standard.
During this process I follow the Microsoft white paper and all appeared to have went well.

2-3 days after the migration was completed and the existing SBS 2008 server was decommissioned external email/push email stopped working. I have 2 iPhones and 1 iPad that were setup to the server via the standard remote.domain.com address that worked fine until that point.

Since that time I have completed the following trouble shooting steps without success:

* Restarted the server
* Deleted and recreated all rules in router
* Completed all windows updates
* Completed all Exchange updates and roll ups
* Purchased and installed an SSL Certificate
* Found an old certificate relating to the old server and removed
* Re-installed the newly purchased Certificate
* Manually installed the certificate on the iPhone devices
* Removed all mail accounts and network settings on the iPhone and iPad devices, recreated the mail account
* Created a brand new account on the SBS 2011 server and tried to connect via an iPhone and iPad device
* Confirmed that when on Wireless (same network as server) mail works without issue
* Confirmed shortly after disconnecting from the wireless mail continues to work for a short period of time but then stops (no changes made to phone or server when this stops can can be anywhere from 5 - 30 minutes later).
* After a server restart mail will work to 1-2 out of the 3 devices but not all at the same time and will eventually stop.

I am literally at wits end trying to resolve the issue and would be very appreciative if anyone could point me in the right direction!!

Tech Specs:
OS: SBS 2011
Exchange: 2010 SP1 Rollup 6
iPhone: 4S on latest update
iPad: 2 on latest update
0
Comment
Question by:Mark Pace
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6 Comments
 
LVL 8

Expert Comment

by:Elmar Koschka
ID: 37732435
Please use the "connect to internet wizzard" and give me feedback...

U can validate here. Post the errors... https://www.testexchangeconnectivity.com/
0
 

Author Comment

by:Mark Pace
ID: 37732450
Hi. Apologies, I forgot to mention.

I have run through all SBS wizards including connect to internet, fix my network and setup your internet address.

Using the testing website, it states all good except a possible compatibility issue with ssl certificates and some windows phones; which is surprising as I can't even hit the external address outside of the network (or inside of the network for that matter!!)
0
 
LVL 37

Expert Comment

by:Neil Russell
ID: 37732469
If your SSL cert is not 100% correct then you will have issues. Do ALL of the possible names match up with the cert? It sounds not.
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Author Comment

by:Mark Pace
ID: 37733854
Thanks for the info. How would I check that all of the names match up and is there a way to confirm my new certificate is 100% compliant with the server?
0
 

Accepted Solution

by:
Mark Pace earned 0 total points
ID: 37735638
After days of searching and changes to the server, it appears that the issue was the router/firewall device.

To resolve I updated the firmware on the device and recreated all rules and email/remote access started to work.

Thanks for all assistance and tips.
0
 

Author Closing Comment

by:Mark Pace
ID: 37756279
Issue was related to router/firewall device on network.
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