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Moving to Ex2010 - ActiveSync not working when proxying or redirecting

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Hi Guys,

Exchange 2007, all roles on a single server and a 3rd party product for the SMTP gateway (MailMarshal) that's setup as a SmartHost in Exchange.

Just built a 2010 box on SP2. Moved a test user across and all mail delivery works fine. All good.

However we have a number of Windows Phone devices that connect via ActiveSync.

activesync.domain.com points to the firewall which NAT's to the 2007 CAS IP. The activesync.domain.com address is specified in the ExternalURL of the ActiveSync config within Exchange.

Works fine on 2007, always has.


However our test user who is on EX2010 is registering with Exchange via ActiveSync, however just sits "syncing" in Outlook on the mobile device. In the IIS logs on the 2007 server I am seeing:

2013-01-18 12:24:35 172.16.8.161 OPTIONS /Microsoft-Server-ActiveSync/default.eas User=test.user&DeviceId=DEBC97F049768F243D0541EF7A260A6E&DeviceType=WindowsPhone&Log=RdirTo:https%3a%2f%2factivesync.domain.com%2fMicrosoft-Server-ActiveSync_Error:MisconfiguredDevice_ 443 domain.local\test.user 213.xxx.169.xx MSFT-WP/7.10.8858 451 0 0 265


The Error:MisconfiguredDevice_443 seems to be a rather good starting point but I'm not getting anywhere in researching it.

I would have thought that the Exchange 2007 box gets the ActiveSync request, realises that the MB is on the 2010 box and proxies to the 2010 DB server. However I can't find any entries for ActiveSync in the IIS logs on the 2010 server....

To confirm, I have two Exchange boxes with CAS, HT and DB roles on it. One is 2007 and one is 2010. 2007 is production and has an activesync.domain.com SSL on it. Client are connecting to it fine, and the ExternalURL is set to activesync.domain.com.

If I have a mailbox on 2010, when the end user connects their client device to activesync.domain.com the user does not get their mailbox downloaded and gets stuck at a "Synchronising" status. Errors then appears in the 2007 IIS logs. The 2010 server is not publically addressable - only the 2007 one is.

Ideally I would like the 2007 server to proxy all requests for MB's that are not local to the 2010 box rather than redirecting (as the 2010 box is not accessible from the internet).

Am I doing something wrong? Do I need to do something special in for the URL's in the Exch config?

Any suggestions?!

Thanks - Steve


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