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Exchange 2010 Autodiscover and Mac

jbmos2333 asked
Last Modified: 2012-05-12
I am converting from SBS Exchange 2007 to a new Exchange 2010 server.  All of the testing was successful and we had a few PC users running on the new server prior to the primary cut over which was tonight.

After making the new Exchange 2010 server live.  I ran into a host of weird problems.   The autodiscover service keeps failing with internal error 500 or says in couldn't be contacted.  Autodiscover is only responded to the internal server name and not the external server name in any of the responses.  And all DNS records (including autodiscover dns) have had the IPs updated to reflect the server change.

Because autodiscover seems to be broken, all testing using https://www.testexchangeconnectivity.com fails.  I have rebuilt autodiscover with EMS multiple times as well as followed the instructions here for a manual rebuild from the exchange CD: https://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_4962-7-Steps-to-AutoDiscover-Heaven.html

I have attached the test-outlookwebservices output for further review.

Ok here is the weird part.  Everything except Mac laptops works perfectly.  OWA works perfectly.  SSL is responding correctly.  Iphones and Droids connect.  PCs connect using RPC over HTTP (Outlook Anywhere).  PC Outlook of course will not auto config, but if you manually add the server settings, it works right.

The EWS with Mac Mail, Entourage, and Outlook 2011 just will not work.  I assume its because everything responds with the internal server name versus the external name when queried.

I have double checked all server settings against another Exchange 2010 configuration that I have and cannot find anything wrong.

Looking for some ideas to get autodiscover working properly and the MACs connected to exchange.  There were no issues with either of these on the Exchange 2007 server.

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