OK… I get it that Let’s Encrypt is free and, “You get what you pay for.”
But why is the documentation so incredibly poor?
Where are the simple step by step instructions for setting up HTTPS for a Tomcat server running on Windows?
Yes I have searched for this information.
I think you'll find that the answer is: because Tomcat makes it a pain in the ass, most people just run a reverse proxy such as Apache or nginx in front of their Tomcat servers.
It is (paradoxically) operationally simpler and means you can perform various maintenance operations (such as installing or renewing SSL) without restarting a (probably stateful) Java application.
The process to use Certbot with Tomcat has been described quite a few times (including by me: issuing a certificate using Tomcat and then installing it to Tomcat) on this forum - but you'd need to adapt the instructions to one of the available Windows Let's Encrypt clients. I'd suggest saving yourself the pain and combining it with a proper webserver - finding instructions for Windows+Apache is a lot more straightforward - such as here.
You can also run a reverse proxy like Caddy which will completely handle all aspects of HTTPS for you and runs on Windows too. You can adapt this tiny configuration file to point to your Tomcat server and domain, and you're finished.
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