Hello Robert,
If I understood you correctly, you are running the Lion’s Server.app on Mavericks. I do not remember the file configuration and I just finished configuring my certificates using “Let’s Encrypt” for my site using the Server.app 5.2 on macOS Sierra 10.12.
I’m using “Let’s Encrypt” and the command line tools; because I wasn’t able to get CertBot to work with my configuration either. I do not expect the support to catch up with the Apple releases just yet so I wrote down the steps and created a job aide. Take a look at it and let me know if you have any questions. Warning: the file paths may be different for your configuration.
Let me know if you have any questions and/or if I can assist you any further.
Kindly
Edwin
Let’s Encrypt for macOS Sierra v10_12 and Server.app v5_2.txt (2.7 KB)