You can play the Playlist, or from the first song if you want that.

Thank you for the quick reply Lowlander! You saying it like that does make me realise it's exactly like "browsing". So it's currently not possible to play a specific song in your playlist and have the entire playlist (aside from that song) be shuffled-played next?
As an example, in Apple Music if I browse to the last song of my playlist and have shuffle enabled, the entire playlist is shuffled and will play after.

Presumably you're browsing files (Artist, Albums, Playlists, ect.) in MediaMonkey. In that case MediaMonkey only either plays the selected file or selected file and subsequent files. So if you intend to play all files you'll either need to select the first or all files.

Hi, I've recently 'updated' to the latest beta from stable MediaMonkey 5. I'm getting accustomed to the new shuffling (rather than the randomization). But I have noticed that when I manually select a file to play, MediaMonkey will only shuffle the files below it, rather than the entire playlist. Per example if I have a playlist of 10 songs in total, and I manually choose to play the 7th file, it will only shuffle the last 8th to 10th file. I am confused if this is the intention and if it possible to shuffle the entire list.

Thanks,
Fentomized