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Apple Mail suddenly can't connect to Exchange over SSL

I swear I will kick myself if this happens again. This is not the first time! I forgot that I had Socks proxy checked in Network preferences! I realized it when not even software update worked. Case closed. 😟


Yesterday around noon my Apple Mail started giving an error, translated into English it says roughly Server "blabla.internal" does not respond, please check your network connection.


This happened without me changing anything in any settings, and persisted. I tried connecting to the server with openssl s_client and that works, I get the cert back but I don't speak Exchange so I can't do much more. I'm the only one at the office with problems and my Windows 7 VMware Fusion guest has an Outlook 2010 that still works fine.


I tried adding my Exchange account into my MS Office Outlook 2011 for Mac but nothing comes up, no errors, no mails. As if it also is having problems to connect.


Why is this only affecting my Mac apps? It boggles my mind.


I tried resetting my entire Exchange account, deleting it and re-creating it, but to no avail.


I even tried sniffing with tcpdump to see if any traffic was going to this exchange server, on any port, and none is! Only if I run openssl s_client -connect exchange:443, then I can see traffic.


Also if I use Outlook in my Windows 7 guest VM, while tcpdump is running in my Mac host, I can see traffic too. This is beyond strange, my Apple Mail and MS Outlook 2011 for Mac have simply stopped sending traffic to my intranet Exchange server.


No one else at the office is having this issue right now.


Also, my firewall is disabled.

MacBook Pro, Mac OS X (10.7.2), MacbookPro6,2

Posted on Jan 8, 2013 12:54 AM

Reply
9 replies

Jan 12, 2013 4:12 AM in response to Pityu Juhász

Pityu Juhász wrote:


I've had exactly the same problem.


I'm a sysadmin for our exchange server 2010.

Yesterday I had 7 new security updates for the server.

That's what caused the problem.

I uninstalled the updates and the problem was solved!

Same problem after 7 new security updates install on 2013-01-09

I've resolved the problem by installing this rollup for Windows Communication Foundation in the .NET Framework 3.5 SP1 for Windows 7 and Windows Server 2008 R2

http://support.microsoft.com/kb/981002


Hope that can help you


Daria

Aug 29, 2013 12:10 AM in response to Pityu Juhász

Hello,


The hotfix isn't working for me. I'm getting an error that the update is not applicable to my computer.


I've installed a few updates yesterday, including the following security updates:

KB2868623, KB2862966, KB2862772, KB2861855, KB2859573, KB2849470, KB2844286.


Besides these updates, Rollup 7 for Exchange 2010 SP2 was installed. I'm now uninstalling the Rollup to see if this makes a differences. After this, I will uninstall the security updates one by one.

Apple Mail suddenly can't connect to Exchange over SSL

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