Let's Encrypt with Windows

It is possible to setup an SSL in a Windows version of an Ignition server? Everything that I can see in the documentation and other forums is for Linux only.

I’m not really following what you’re saying but hopefully starting here helps you out: https://docs.inductiveautomation.com/display/DOC80/Using+SSL#UsingSSL-EnablingSSL

Sorry should have been more clear in the description. I’m wondering if anyone has successfully setup an SSL certificate with Let’s Encrypt on a Windows Ignition Server. All of the literature/examples that I can find are only for Linux.

You absolutely can set up Let’s Encrypt on a Windows host - you’ll find that most guides follow Linux because it’s somewhat simpler to set up, but there’s absolutely nothing stopping you. It’s important to separate a few things:
Let’s Encrypt is a new CA (Certificate Authority) and one of/the first CAs to support the ACME protocol - as the acronym implies, it’s all about automated certificate management. ACME/LE push towards a new style of short-lived, automatically renewed certs; ‘legacy’ SSL certs generally last so long (2, 3, 5 years) that it’s not worth the effort to automate. By only issuing short lived certs, LE incentivizes automation.
In addition to Let’s Encrypt, you’ll often see something called certbot - though it’s usually not called out as a separate “thing”. certbot is an ACME ‘client’, and it absolutely has support for Windows:
https://certbot.eff.org/lets-encrypt/windows-other.html - but, you really just need any ACME client to use Let’s Encrypt - certbot is just the “reference” implementation. For instance, there’s a variety of IIS implementations: https://letsencrypt.org/docs/client-options/#clients-windows-/-iis

Once you have an ACME client, a lot of the rest of the SSL guide here should still apply - you’ll have to change the command line arguments a bit, but the basic process is still the same.

@PGriffith we’ll give it a try as you describe. Many thanks!

I have used Certify the Web successfully on a Win2016 server: