I’m new here!
So, I work on a IT Service Provider, we have Spiceworks running as our ticket system. Currently we use certificates issued by StarSSL but they have problems with the intermediate certificates, yes I know, I’m not using the SHA1 anymore.
Spiceworks is Windows only and runs over Apache, but all the Python clients are *Nix based.
We also run the server on a non-standard port, HTTPS 443 is not used, we changes it to 7070, both for communication with the remote collectors and we have a local cloud system already using that port. I don’t know If I will have problems using Let’s Encrypt.