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Certificate Basics for Small business server 2011

Posted on 2016-10-17
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Last Modified: 2016-11-06
HI all,

Im new to installing an actual real certificate on a server and am not sure how to go about it. I know how to actually install it, its just the topology is confusing me

I have a registered domain which lest say is abc.com
I have a mail server on hosted in my office which is using a dynamic ip. I have registered a hos name with no-ip which lets say is abc.ddns.net
The mx records for abc.com point to abc.ddns.net
Everything works fine.
In attempt to get rid of errors associated with self signed certificates i thought i would try and install a certificate, however im not sure how i order this certificate under this topology.

When i generate the request, as the SBS server is set up with the external domain of abc.com, it generates the certificate request with the common name of remote.abc.com. However users will actually connect to the server by entering abc.ddns.net. Will this cause a problem?

Any advice for this scenario welcome
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Question by:Michael
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by:David Johnson, CD, MVP
David Johnson, CD, MVP earned 250 total points (awarded by participants)
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yes it will generate an error as the name doesn't match the name on the certificate
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by:Cris Hanna
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Is there a reason they can't get a static in?

My only other thought would be that go to external DNS records  and modify the A record for remote. domain. com to point to abc. does.net
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Simon Butler (Sembee) earned 250 total points (awarded by participants)
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I have done this loads of times. Ran my own Exchange server with a dynamic IP for three years (no other choice at the time).

Using the domain that you own, create a CNAME for remote.example.com and put it on the DNS of the dynamic IP address provider (site.dyndns.com). You can do the same for Autodiscover.example.com. Not exactly best practise because it involves an additional DNS lookup, but for an SBS server it should be fine.
Then request an SSL certificate for remote.example.com in the usual way.

With SBS 2011 though, it has to be done in a certain way to work properly.
Create the certificate request through Exchange, not SBS. That way you can include remote.example.com and Autodiscover.example.com (using a UC type certificate). Then once you have received the response and completed it, use the SBS certificate wizard, choosing the option to use an existing SSL certificate.

http://exchange.sembee.info/2010/install/ssl-sbs2011.asp
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by:David Johnson, CD, MVP
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Sembee's answer fixes the problem
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