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Self Signed certificate problem

Posted on 2014-07-18
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Last Modified: 2014-07-18
This is SBS 2008. Our self-signed certificate expired yesterday. I have used the 'Set up your internet address' wizard in the SBS console. I can see the new certificate is there, and it expires in July 2016.

My problem is that the client pc's dont seem to trust it. When anyone opens Outlook they get a certificate error stating that the certificate was issued by a company we have not chosen to trust.  When I look at the certificate, it is issued to remote.myexternaldomain.com and it is Issued by internaldomain-server-CA I've checked the expired certificate and it has the same information. So how do I fix this?
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Question by:TownTalk
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4 Comments
 
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Assisted Solution

by:Alan Hardisty
Alan Hardisty earned 500 total points
ID: 40204032
Install the new certificate onto every machine you have or buy a trusted 3rd party SSL certificate for $60 a year and then it will automatically be trusted and you don't have to install anything on any machine other than the server.
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Author Comment

by:TownTalk
ID: 40204034
But the self-signed should be trusted shouldn't it? I didn't have this problem when I re-issued the certificate 2 years ago.
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LVL 76

Accepted Solution

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Alan Hardisty earned 500 total points
ID: 40204048
When the clients join the domain, the certificate gets installed onto their PC so it therefore trusts the server because it has the certificate installed.

Now it doesn't have the new certificate installed, so it doesn't trust the server.

Not sure what you did 2 years ago, but that's what you need to do.

Alan
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Author Closing Comment

by:TownTalk
ID: 40204153
Ah yes I understand now. Most of the machines are less than 2 years old, so they would have got the certificate when they were joined to the domain.  I've been around and installed the certificate, and I found that the problem wasn't occurring on the machines which are older than 2 years. So for whatever reason, they trust the certificate. I'm curious as to why this is the case, but my problem is fixed. So thanks guys for your input.

Ian
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