>Running a VM once a month just to renew my 3 certs is a huge headache. Not overly familiar with Windows administration (or the tools available to work with SS

>Running a VM once a month just to renew my 3 certs is a huge headache. Not overly familiar with Windows administration (or the tools available to work with SSL/TLS stuff), but you can use Docker to automate basically all of that; IIRC it's supported on Windows now. >Not to mention the whole process is so very incredibly fugly. On the contrary, the process is pretty simple, even if you're going fully manual! 1. Generate a CSR for the domains you want to register 2. Place a proof of ownership somewhere on your server in a way that Let's Encrypt can verify it's there 3. Contact LE's API and tell it what domains you want to register, what you want to get signed, and where your proof is 4. Get a signed cert back. The rest is just server configuration to point to the cert. If you use something like `certbot-auto`, it's basically a GUI step-through process.