As Zac says, I learned that the SSL option in the Lucee admin is for some sort of inter-server communication setup.
For SSL to your server you need to figure out how to get and install certificates in your web server (Apache, Nginx, TomCat or IIS).
I had a small server running Lucee with TomCat. It seemed to work pretty well but seemed somewhat limited especially with regard to multi-hosting. There are no doubt people who could do that blind folded.
Apache seems well suited to acting as the front end web server for Lucee. It’s vastly configurable and there’s quite a lot of support online for Apache. I found many articles on how to setup SSL to work with it.
I find Lucee with Nginx to be easy to setup and configure. It seems to perform very well. Also you can skip mod_cfml during Lucee installation (not needed). August Kleimo posts on Lucee with Nginx were super helpful.
With regard to your specific question I did get SSL working on each type of web server except TomCat. My current Favorite stack is Lucee/Nginx on a small AWS ec2 Linux instance. I put Elastic Load Balancing in front of the instance to get fail-over and auto scaling. Its quite inexpensive and powerful. I connect AWS Certificate service to ELB so I don’t need to install cert(s) on the server(s).
I know I ranged wide in my response but you never know what someone might find helpful.