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Smart playlists played on iPhone not updated in MacOS music app  

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Hi, Friends,

I manage music on my iPhone by creating smart playlist in the music app (formerly known as iTunes). The playlists are populated by least recently played, so when I play a song it falls out and a new one is added in. In the past, when I played music on my phone, the playlists would update both phone and iTunes when I synced my phone. Now, songs played on my phone are not updating the playlists in the Music app.

I just updated to Catalina, but the problem had started before the update.

 

Any ideas?

Thanks!!!

 

iPhone 11 Pro running iOS 13.4.1

iMac (Retina 4K, 21.5-inch, 2017) running macOS Catalina 10.15.4 (19E287)

EDIT:
I'm old school and sync to iTunes (now music) with a cable. The cloud is not involved.

This functionality worked well for years and only recently stopped. 

My goal is to have a rotating set of songs on my phone (50 in a few different genres added by least recently played) since my entire library won't fit. 

I do not have an Apple Music subscription, thought I do have iTunes Match.

1 Answer
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On my Mac (10.13) any playlists I make that are “dynamic” have a symbol next to them indicating that the playlist won’t sync to the cloud. This was discussed years ago on apple’s support forums, with the conclusion that Apple didn’t have a way to deal with dynamic playlists in their cloud. Which kind of makes sense...  if the criteria/logic for the dynamic playlist are stored on your Mac, it would be pretty tough for Apple to somehow replicate this logic in the cloud. 

@cpragman
Thanks for the answer. Sorry for being unclear. I'm old school and sync to iTunes (now music) with a cable. The cloud is not involved.

This functionality worked well for years and only recently stopped. 

My goal is to have a rotating set of songs on my phone (50 in a few different genres added by least recently played) since my entire library won't fit. 

I do not have an Apple Music subscription, thought I do have iTunes Match.

Thank you!

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