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SSL Certificate Import in SBS 2011

Posted on 2011-09-26
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Last Modified: 2013-12-02
I am doing a migration from SBS 2003 to 2011. I have followed the MS instructions to export my trusted SSL certificate from the old server and copied it to the new one.
If I browse to the Computer Personal Certificate store I can see the certificate in there, however when I run the Add a Trusted Certificate Wizard and browse for certificates it does not appear in the list.
Any ideas?
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Question by:nealerocks
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by:Cliff Galiher
ID: 36699932
Exporting and importing is tricky. You have to get the private key, get it in the right store, get the system *exactly* as expected for the wizards. Time consuming and error prone. Skip it. Use the certificate to generate a new CSR (and, by proxy, private key), then use the "rekey" option of your public CA to generate a new certificate. Rekeying is free, as far as SBS is concerned, you used the wizards as intended, and it is almost foolproof for a successful cert. Much better than the export/import game.

-Cliff
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by:nealerocks
ID: 36708376
Thanks for the suggestion. I will give this a go tomorrow.
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by:nealerocks
ID: 36714804
I generated a new CSR request and rekeyed my certificate but it still doesn't appear in my Add a trusted certificate wizard.
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Expert Comment

by:Cliff Galiher
ID: 36714808
HOW did you generate the new CSR?
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by:nealerocks
ID: 36714827
I used the new exchange certificate from the exchange 2010 management console
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Expert Comment

by:Cliff Galiher
ID: 36714974
No. Stick to the SBS wizard. Use the add trusted certificate wizard to generate the CSR (the first option in the wizard) then rekey with that CSR, then rerun the wizard to import the cert (the second option in the wizard.) it is designed to be run twice and manages properly pairing public and private keys. By skipping the first run during the CSR phase, you are just confusing the wizard.

-Cliff
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nealerocks earned 0 total points
ID: 36715090
I managed to get around it by installing it directly into exchange rather than the wizard.
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Author Closing Comment

by:nealerocks
ID: 36899025
Figured it out myself.
Thanks for the suggestions.
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