I realise everyone is probably screaming in horror at the above combination, but I am trying to help a completely blind friend with his learning/hobby sites (two domains).
For better or worse, this is the software he is happy with on his remotely-hosted dedicated server. I have tried reading various blog posts and they all refer to IIS on Windows Server. I also see that there have been quite a few recent updates surrounding ACME V2 in the last couple of days.
I have a fully working Cerbot on Ubuntu, and one thing I was thinking of was getting him to temporarily point his DNS to my server, then grab the cert, then send the bundle to him… but then, is the generated cert going to be compatible? It needs to be completely valid!
I know really nothing of Apache on Windows, but he seems familiar with it. Any suggestions? Thanks.