Seth - I understand. Oh, how I wish someone had already written a Windows client.
Andrei - Okay, I ignored the SAN part of the .jks file generation and I assume that means I’ll leave off the -ext part of the CSR generation.
For anyone following this, I am referring to: Tutorial - Java KeyStores (JKS) With Let's Encrypt. Andrei - let me know if I should ask my questions there instead of here.
My next question: Where in the world did you get certbot for Windows? I assume from the (PowerShell?) screenshots that you are working in Windows? I resorted to cmd.exe, in case that matters.
As you may recall, I did find letsencrypt-win-simple\letsencrypt.exe. Perhaps that will do the trick? I’d just prefer something simpler. letsencrypt.exe seems not to support DNS challenge so unless I get figure out, or get help with, instructing le-win-simple how to challenge JIRA/Tomcat, I’ll have to: stop JIRA, fire up a temporary web server, do the challenge and then do the reverse (and automate that for renewals).
Not to complain but this seems to be incredibly “challenging” (pardon the pun).
Thanks for your continued support.
Craig