Music.app Shuffling
However, getting that playlist working this year proved intensely frustrating. Even though it contains over 300 songs, only a handful played when we asked Siri to shuffle the playlist on the HomePod. It made no sense—I could cause any song in the playlist to play on the HomePod from my iPhone, and the Music app had no problem continuing from one song to another as long as shuffle wasn’t turned on.
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But wait! Isn’t there some other checkbox that might be related? I opened the Info window for one of the tracks that wouldn’t play and clicked through all the tabs. There it was in the Options tab: “Skip when shuffling.” I selected all the songs in the playlist, pressed Command-I to open an Info window that would apply to everything selected, and turned off “Skip when shuffling.” Voilà! My playlist started working correctly again.
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But this raises a question. If you prefer to listen to holiday music only at the end of the year, how do you prevent it from playing at other times? I can imagine a range of approaches, including exclusionary playlists and separate music libraries, but they would require me to change how I interact with Apple Music for the rest of the year. Other techniques suffer from allowing holiday songs to be mixed in with other music.
I’ve been seeing some strange behavior recently when I tell the Music app to shuffle a particular artist. I would expect this to produce a random-seeming mix of all the songs I have by that artist. But often it actually plays one of the following:
- A random mix of songs, but only from the artist’s most recent 2–3 albums, when there are far more in my library.
- A random mix of songs, but each time it plays a song it will play all the versions of that same song (e.g. compilations, live recordings) before moving on to the next song.
Update (2025-12-18): Wayne Dixon:
I’ve been seeing an issue with shuffling myself. I’ll listen to a bunch of shuffled songs, switch to some other audio for a while and when I listen again, it will replay songs I’ve already heard.
Now, I don’t know if it’s strictly something that’s related to moving from my iPhone, to a HomePod, and then back again. It will continue what I was listening to on the HomePod, but after switching to other audio and then back again, it seems to jump back in the playlist.
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This year my HomePods decided to shuffle only by album/artist. Giving them a playlist of favorite songs, the shuffled order produces clumps of songs by the same artists.
On iOS or Mac, one can go to the list of Songs and simply press shuffle. HomePods will not shuffle an entire library, but just sit there, light pulsing helplessly.
A long time ago (probably 2 decades at this point), in iTunes on the Mac, I created a smart playlist to play songs that I haven't heard in a while. It randomly selects 2 hours worth of songs whose "Last Played" time is at least 6 months ago. On the Mac, this playlist contains an assortment of songs from various artists/albums. The iPhone, on the other hand, seems to populate this playlist by randomly picking an album, adding ALL eligible songs from that album, then picking another album, etc.
