Once Thanksgiving is over, Tonya and I like to play holiday music from an extensive playlist we’ve built up over the years. 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. Other playlists worked fine, but there was no apparent difference between them and the holiday playlist. Nor could I get the playlist to shuffle on my iPhone or Mac.
Finally, I rolled up my sleeves and started poking at the playlist in the Music app on my Mac. Thinking that the source of the songs might be related, I created a version of the playlist that included only Apple Music tracks, excluding those purchased from the iTunes Store. No change. I then tried creating new playlists from small subsets of the main playlist, but clicking Shuffle didn’t play anything from those playlists. Grasping at straws, I created a smart playlist that collected songs by genre and album title. Despite having 70 artists in the playlist, all the songs that appeared in the Up Next queue from shuffling came from fewer than 10. Then I remembered that the Music app has an option to ignore unchecked songs, so I turned on Music > Settings > General > Songs List Checkboxes, but it only showed everything as checked.
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.
Upon reflection, this was a self-inflicted problem. Much as we enjoy holiday music for a few weeks in December, it gets old by January, and it’s downright irritating to have it pop up randomly any other month of the year. “Winter Wonderland” isn’t amusing in August. So last year, in an effort to prevent holiday music from playing outside the holiday season, I enabled “Skip when shuffling” for the entire playlist. I likely stumbled upon and added a few promising songs and albums afterward, which would explain why a small number of tracks were unaffected. Had I merely left myself a reminder for December 1st to reverse the option, all would have been well.
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. For instance, I want to listen to everything that Dave’s True Story has recorded throughout the year, apart from their Christmas album, but I don’t want to lose track of the fact that I like the Christmas album in December. Similarly, if I ask Siri to shuffle my entire Apple Music library in June, I don’t want any holiday music sneaking into the mix. What’s your solution?
