SSL cert setup for Wiki on OS X Server

Server
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Success! The live .sh file generated the necessary files and I was able to assign the Let’s Encrypt certificate in the Server app!

To recap, in hopes this may help others:

This tutorial is helpful to download and install a certificate from Let’s Encrypt for a website (in my case, a company Wiki) hosted on a Mac with Server app. There are three edits that you should be aware of, though:

  1. As of OS X 10.11.6 and Server 5.2, the default root directory for the Wiki (and likely other websites hosted by Server) is /Library/Server/Web/Data/Sites/Default

  2. Line 3 of the get_cert.sh file needs to be edited so that no space exists between the equal sign and the value(s) you enter for YOUR_DOMAIN.

  3. Make sure the cert.ini file is in the working directory of the commands your executing in Terminal. The easiest method for that is probably just to cd to the folder which your cert.ini and get_cert.sh files are stored.

  4. As mentioned by @schoen, upon creating the get_cert.sh file, run the command chmod +x on the file to allow it to be executable. Run the same command on any copies made of the get_cert.sh file, for instance if you have one .sh file for dry runs and another for a live run.

Hopefully, this will be helpful to others.

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So, hopefully this is the last issue. The certificate is generated, it shows under Certificates in Server.app, however when I attempt to select the certificate, I receive this prompt:

Except, I never get a prompt to enter a password, when I press Continue. I’ve attempted to restart the Wiki and Website services, Server.app, and the Mac Pro all of this sits on. Is the private key within Keychain Access that I could perhaps edit it’s permissions?

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The answer is yes, the private key can be accessed and edited within Keychain Access.

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Glad you finally got everything working, @WilhelmSturmer.

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