The behaviour you see is the expected behaviour when selecting at the song level. If you want to operate on the playlist as a whole, use the blue button at the top left of the screen
I just want to add that the blue buttons can be arranged on the Settings/Play Action screen. There is setup for both Playlists as a whole and Playlist on a track level. At the track level, as you have seen you can play from or queue from here; but, not the whole playlist (unless you are on the first track).
Which is ridiculous. Why can’t I play my playlist by clicking a track. Every other music client supports this that I can think of, and I’ve used Tidal, Spotify, Qobuz, Pandora, etc.
Seems strange that this wouldn’t be the default behavior. If I want to play a specific song to start my playlist with my queue in shuffle mode, I should be able to. Instead, I have to add my song to queue, queue the playlist, and then go back to the queue and start from here on the song I wanted to start with.
Remove the duplicate song from the queue by clicking the queue button and then finding the song, clicking the song, and then another click to remove from queue
In Roon, clicking on tracks is for track based functionality…
What you wish to do is shuffle the whole playlist … to do this use follow the advice given by Brian …
The default action is to add the playlist in order to the queue… a lot of people want this.
To shuffle it, just click the small down arrow and select shuffle… 2 clicks job done.
Note: if shuffle is your thing … the default action can be configured to do this in settings.