@sngmorris Nice to see you around the community. To shuffle a playlist: Navigate to your playlist in your collection. Click on the Shuffle icon located to the left of the Play button. When the shuffle icon is highlighted, it will shuffle all the songs from that playlist. Here is a photo of where that is located on your computer:   If your playlist is already playing, you can also Shuffle it directly from the Now Playing screen: Go to the Now Playing screen and select the icon with intersecting arrows on the bottom of the screen to turn Shuffle on or off. When the shuffle icon is highlighted, it will shuffle all the songs from that playlist. Here is an example of where that is located when listening on your computer: I hope this hepls! ... View more