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Certificate Expired error thrown up by SBS2008 BPA

Posted on 2014-11-14
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Last Modified: 2014-12-13
We have a SBS 2008 and would like to do a migration to 2012 Essentials. When we run the SBS Best Practices Analyser on the SBS 2008, we get the following critical error:
"The ssl certificate for https://Companyweb:987 expired on 10/19/2011".
Following advice on some forums I ran the "Add a trusted Certificate" routine in the Windows SBS Console choosing "I want to use a certificate that is already installed on the server". It went through successfully and reported "The trusted certificate is imported successfully"... but still getting the same error in the BPA.
What do we have to do to renew this certificate. Can we continue the migration without renewing the certificate? Usually these 'red cross' errors mean no you can't.
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Question by:laurencoull
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by:becraig
ID: 40443654
You can just renew the self signed certificate and then add that certificate to Trusted Root.

HEre is a how to on renewing the certificate:
http://www.kbtechnical.com/Blog/tabid/178/EntryId/5/Renew-SSL-self-signed-certificate-in-SBS-2008.aspx
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by:laurencoull
ID: 40443857
Ok that sounded easy but it told me before running 'setup your Internet address' I had to firstly run the Connect to the Internet wizard, which failed with "Windows SBS did not properly configure your email". This seems to point to issues in MMC which I think will be troublesome to resolve. I'm not concerned about renewing the certificate if the migration process will allow me to complete it with these certificate error conditions in the BPA. But will it?
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becraig earned 2000 total points
ID: 40460183
You should be able to complete even with an expired certificate, however you can create a self-signed certificate in IIS with the name: Companyweb

Then simply add it to the trusted store and re-run.

Here are the steps for creating a self signed cert in IIS
http://technet.microsoft.com/en-us/library/cc753127%28v=ws.10%29.aspx
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