How to issue certs for Windows servers?

Hi!

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.

well you could make the certs using manual mode on an independent unix mavchine or if your 80/443 arent blocked you could even try to redirect the traffic going through those to the unix machine and run LE in standalone, making the validation automatically.