The shuffle button use to be able to toggle if the current queue was shuffled. Now it seems to do nothing whether the queue is shuffled or not, just greyed out.
This seems to depend on what you’re playing. Radios, mixes for you, sonic adventures etc. are created based on a certain logic; you cannot simply reshuffle those.
If you play items from your library individually, you can enable / disable shuffle without any issues (this will also cause the queue to reshuffle)
In addition, server prevents shuffling when there is an “up next” region, meaning you’ve modified the queue. There is an implicit version of this when playing an album ~ Play Queues | Plex Support
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