The "Start playing when files added to Playing Now" feature hasn't been working for me at least since MC 27.0.62, and it still doesn't work in 27.0.79. When I add a file to the end of playing now, when player is not playing, via any of these methods:
-- right click and select "Add to Playing Now"
-- double click, when configured so that this adds to end of Playing Now
-- add to Playing Now with JRemote
...the selection gets added to Playing Now correctly, but the player doesn't start playing. If MC has been sitting idle for hours, sometimes the feature works once. But inevitably, if I pause and try it again, it fails.
The "Start playing when files added to Playing Now" option is definitely enabled; I toggled it to be sure, restarted MC, updated to 27.0.79. The feature is not working for me now; I had been using it successfully for years.
Mac Mini, macOS 11.2.3
MC 27.0.62 and 27.0.79
JRemote 3.36 on iPad