I have installed letsencrypt on a macOS Sierra server according to this tutorial by @JeffTheRocker : Complete guide to install SSL certificate on your OS X server hosted website
Everything seems to be working just fine, including the check via .well-known. However, after renewing, a seperate (duplicate) cert is added to keychain and the Server app, not replacing the old one, and is not automatically activated. So, currently, I still have to manually change the certificate every 3 months.
I have found this possible solution by @cyrilpic : Mac OSX (Server): import LE certificate?
The linked script (https://gist.github.com/cyrilpic/4504527de3a7b08ed84e) seems to include all necessary commands to fix renewing, however after some hours of trying I have not succeeded in combining the renewal script from the tutorial and the github-linked one.
Some help would be greatly appreciated! Thanks a lot.