I'm experimenting with this too and it isn't working for me either.
Using Windows, I have my tiddlywiki in a folder called mywiki.
csr.pem, key.pem and server.crt are ALL in the mywiki folder
using this command to start:
tiddlywiki mywiki --listen tlscert=server.crt tlskey=key.pem host=0.0.0.0 --verbose
I get:
(press ctrl-C to exit)
Boot log:
Startup task: load-modules
Startup task: info after: load-modules before: startup
Startup task: startup after: load-modules
Startup task: story after: startup
Startup task: commands platforms: node after: story
syncer-server-filesystem: Dispatching 'save' task: $:/StoryList
filesystem: Saved file C:\Users\skingery\OneDrive\TiddlyWikiNode\mywiki\tiddle
rs\$__StoryList.tid
So it is working on plain ol' http but not on https. Assuming I created the certs correctly, what am I missing?
tiddlywiki --version
5.1.19