Let’s Encrypt SSL on Windows

My Windows servers are already running Apache with several live virtual hosts, and I have full administrative access to each machine. I now want every domain and sub-domain secured with a single, automated Let’s Encrypt (or similar ACME) solution that renews itself without manual intervention.

The job is to:

• Install and configure an ACME client—win-acme, Certbot, or another proven tool—so it works reliably on Apache 2.2 and 2.4 across multiple servers.
• Issue one or more SAN certificates that cover all existing sites, confirm they serve correctly over HTTPS, and set up scheduled, zero-downtime renewals.
• Produce a clear, step-by-step document (screenshots welcome) that shows how to add future domains or spin up a new server with the same process.

I will test by spinning up a new vhost and following your guide; everything must finish with a valid, green-padlock HTTPS connection and an automated renewal task visible in Task Scheduler.

If you have done similar Windows-based Let’s Encrypt roll-outs before, this should be straightforward. I can remote access as soon as we agree on the timeline.