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Exchange Cert and Outlook 2010-07, problem with users connecting

Posted on 2010-08-27
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Last Modified: 2012-05-10
Alright guys, here is another one for you. Exchange 2010 certificate and Outlook 07-10. Last week Android released a new update for their phone so naturally all my users decided to jump on the bandwagon and installed it; Bad news for me because now their phones will not connect to our exchange server from the outside. See I was using the default certificate that came along with the exchange server, labeled as MYEXCHANGESERVER.MYDOMAIN.local. So I got on the phone with the guys at Sprint (our carrier for the Android) and they tell me that I need to buy a cert for my Exchange server, seems it doesn’t like anything other than “A real certificate”, despite my arguments with Sprint about my “Legit” cert I decided to get one from Godaddy. I installed the cert and off I went, worked great. But…….. then comes the nightmare. All my outlook users start to get a message about it not trusting the new cert. Obviously because it is registered as the outside address and my internal users are connecting to Exchange from its local address. So I start the process of installing the new cert and what do you know! It doesn’t work despite the message stating that it was imported correctly. So here is my problem, at this point I have either working email on phones or an annoying message on Outlook.
Under Exchange I got into the new certificate and enabled it for everything except IIS and now the phones error out but the local users can access Outlook. Does anyone have any ideas?
Here is what I’ve done.
Went into the database of local certs (internet options – content) and tried to remove cert. No go
Went and tried to add manually pointing to the actual cert file. Says it was successful but does not list
Checked my domain cred, I am Master of everything including this PC.
Checked if I was added to local admin. I’m there
Deleted my Exchange account under “mail”, restarted Outlook and ofcourse there is no SSL cert error
Added my account and restarted Outlook, same problem
logged off and into local admin, setup outlook and!!! HEY no problem!! But its still building the ost file
What else can I look at?

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Question by:Willsadventures
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kpoochi earned 500 total points
ID: 33544937
To make it simple..... get your phones working and let Outlook give cert error

To resolve the cert error in Outlook follow http://support.microsoft.com/kb/940726 to change the URL's to the name on the certificate.

Follow the article and you should be able to resolve the issue
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by:Willsadventures
ID: 33545278
Perfect. I was look every where for that D#@N command.

Thanks buddy!
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