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Why?
I know there are other methods such as reverse proxy or simply running a different web server but I think this is a simple and intuitive alternative which could make life easier for non-insignificant amount of server owners.
Drawbacks
Letsencrypt issues certificates for 90 days, and even the longest-lasting certificates are 398 days at most, this number shrinking to 47 days by 2029. Thus, the process of generating a keystore file and placing it into the plugin data directory could need to be automated, perhaps by a bash script, or we could eventually look into auto-renewal strategies using ACME and Letsencrypt.
The following would need to be added to docs/wiki:
In the folder containing your .pem certificates from Letsencrypt or any other provider, run this command:
openssl pkcs12 -export -in fullchain.pem -inkey privkey.pem -out keystore.p12 -name undertow -password pass:to generate
keystore.p12file, which you can then place in/plugins/squaremap/folder and restart the server. Voilà