Erik, I suspect we'll hear from others on this, but I noticed what I believe is the same behavior on my system, and perhaps it was a change made during a recent update.? When you open your Roster, click on any entry and you'll see that the buttons at the bottom right will transition from "greyed out" to "active."? It was a head-scratcher for me until I found the solution, and I recall restarting JMRI several times before I discovered it.? HTH!
John?
Swanny