Sunday, September 16, 2012

OS X Mountain Lion Webserver SSL nightmare

I'm having an issue with OS X Webserver that I'm trying to figure out with Apple. Apparently many other people have also been having SSL issues when using, since before Mountain Lion.

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  1. So there was an update for ML released on the 19th ( but still no fix for the issue I reported to Apple. The tech I was on the phone with seemed very convinced that it was a bug in ML. Personally I'm sure it's a bug - but still there is no fix for it.

  2. I got a call back from from the gentleman that I opened the case with earlier - but unfortunately I missed the call. I am waiting for a call back with good news. If Apple gets this fixed, I'll have the green light I need to start deploying OSX-ML servers. My typical solution stack involves deploying Atlassian Confluence, though I am quite surprised that officialy Confluence is not supported on OSX Server - yet.

  3. I am finding that a lot of people consider OS-X Server to be joke. I would have to say that at this point, I tend to agree. Apple still has a ways to go before OS-X "Server" is enterprise ready. I currently administer Windows and Linux servers and I don't get nearly half the headaches from them that I get from OS-X Server.

  4. Here's a reply I got from another user with the same issue (since Apple never came up with a solution):
    "I started with a certificate and key pair plus an intermediate certificate chain, all as strings from my CA's website. I created text files out of them, then merged them together into a .p12 file so Keychain Access would import them. Everything looked OK to me, but the Certificates panel in the Server app wouldn't assign that cert to the web server process. Same result as you described.

    On a hunch, I deleted the cert and key from Keychain Access and added it through the Server app's Certificates panel. Its drag-and-drop interface guided me through uploading the three files together. After that, Server had no problem assigning the new cert to all of its managed services." --