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Helpful answers
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Feb 28, 2016 11:05 AM in response to ElB1by MrHoffman,Multiple-domain certificates have been available for some time — you only need one IP address, and this greatly simplifies certificate management.
These multiple-domain certificates are sometimes called Universal Communications Certificates, or UCC certs.
One IP address, multiple domain names.
FWIW, the folks at LetsEncrypt also support "regular" and these certificates, and offers free certificates.
If you want to research the problem, you're going to need to have a look at the logs via Console.app or other tools, and try to gather more details on the error. With Server.app, I'd tend to use MD / UCC certs, too — but otherwise, you're going to have to get all the certs and all the private keys registered, and figure out what's tipping over within (presumably) Apache. (I've seen Apache tip over with various errors with OS X Server, and in one recent case "unexpected" characters in the filename for the certificates.)
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Feb 28, 2016 6:12 PM in response to MrHoffmanby ElB1,Thanks for the reply, but the problem turned out to be something else completely.
It turned out that, unlike apache 2.2, apache 2.4 doesn't like it when you put the directory of a site inside the directory of another site. We had the the DocRoot of the secure domain inside the DocRoot of the non-secure domain, and somehow the only visible error was problem with .htaccess file.
We separated the folders to the same level and all was resolved.