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Exchange 2010 SSL not being accepted by Outlook on our Server 2003 RD hosts. But does on Server 2008 R2 hosts.

Posted on 2015-01-19
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Last Modified: 2015-02-10
We have an issue on our Server 2003 Remote Desktop hosts. All users are prompted with an error about not being able to load the SSL.

ssl1
Users on our Server 2008 R2 Remote Desktop Hosts do not see this error & the SSL loads correctly.
Both host OS versions are running Office 2010 & they connect to the same Exchange 2010 Server.

Every user on the Server 2003 farm is prompted with this error every time they load Outlook.

We did recently renew our Exchange SSL in December, this seems to be when the issue first occurred.
I am guessing either the certificate file is corrupted or the renewal/new download is no longer compatible with either Server 2003 or IE8.

Any help would be greatly appreciated.
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Question by:Howzatt
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by:David Johnson, CD, MVP
David Johnson, CD, MVP earned 222 total points
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when last did you update the root certificates on the server 2003 machines?
Update your root certificates and ensure that the 2K3 machines have the intermediate certificates from your certificate provider

http://support.microsoft.com/kb/931125
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by:Gaurav Singh
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please check the connectivity on below URL:

https://testconnectivity.microsoft.com/
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by:Howzatt
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info on updating the root certificates seems a bit sketchy for Server 2003.
The MS update for it has been pulled and all the documentation about it talk about Windows XP.

I'm pretty sure this is the issue though as our Server 2008 R2 hosts are unaffected. Apparently the root certificates update automatically in 2008 R2.

Just struggling to find the clear instructions for users who did not previously download the Windows update fix for this.
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by:Gaurav Singh
Gaurav Singh earned 110 total points
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Hi which CA's Certificate you are using?
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by:David Johnson, CD, MVP
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you can get the intermediate certificates from the Certificate Authority
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by:Howzatt
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CA I thought was Go Daddy. But it is saying it's Starfield now? Did they change their name?
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by:David Johnson, CD, MVP
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starfield is godaddy
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by:Howzatt
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I don't understand what it is that I need to get from them?
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by:David Johnson, CD, MVP
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Intermediate Certificates if your certificate was from starfield get the starfield intermediate ones
https://certs.godaddy.com/repository
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by:Howzatt
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And I install on the Server 2003 Remote Desktop hosts?
If so, tried that and it didn't help.
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by:Simon Butler (Sembee)
Simon Butler (Sembee) earned 112 total points
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If you haven't updated the root certificates, then you will probably need to download and install BOTH the root and the intermediate certificates from the GoDaddy/Starfield repository. Ensure that you install them in the Computer context in Certificates Manager and not Personal.

Simon.
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by:Howzatt
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How do you do it from the computer context?
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Simon Butler (Sembee) earned 112 total points
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When you run MMC, and choose certificates, you get a prompt. One of those is Computer.

Simon.
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by:R. Toby Richards
R. Toby Richards earned 56 total points
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I had a similar issue trying to set TLS in group policy. My problem was that 2003 can't install a version of IE that understands newer SSL/TLS protocols. I was able to get around the group policy by futzing with administrative templates. Unfortunately, your issue may be more difficult to resolve. Are you sure you are using SSL, not TLS?
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