For some reason Android Auto doesn’t want to shuffle my playlists when I am driving and I don’t feel like listening or jumping through a dozen of the first songs on the list that I’ve listened to recently.
Unfortunately Google doesn’t provide us with an option to shuffle a playlist in place like decades old technology such as WinAmp has. But I’ve found a workaround, before I go on a road trip I load up my playlist page, click the shuffle button, this will start playing your entire playlist in a random order. Then you can save your Queue as a new playlist. Pretty simple, and it works if a bit cumbersome. I just delete these temporary playlists when I am not driving.
Unfortunately the Queue is limited to 1,000 songs, but since I treat these as temporary playlist for when I’m travelling I don’t really see it as a problem, though I’d really wish Google would just implement a way to shuffle your list in place.