iTunes Match won't Download Entire Playlist

Aragornii said:

Any ideas?

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No. But I've had exactly the same experience.

Aragornii said:

I have iTunes Match and want to download all tunes from certain playlists to my iPhone so that I have access to them locally rather than streaming.

If I hit "Download All" at the top of the playlist, it only downloads the first 25 songs and the rest just have a spinning red circle. The only way to download the remaining tunes is to manually tap each spinning red circle to get it started, which isn't practical with a playlist of 1,000+ tunes.

Any ideas?

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Have exactly the same problem. Have tried a restore from backup too. This didn't help either - https://forums.macrumors.com/threads/1786762/

Nested playlists

I had this issue too on my iPhone and iPad, and tried a bunch of different things and nothing worked. Then I discovered that songs in playlists within folders in iTunes wouldn't download, but non "nested" playlists worked normally. I made all my playlists flat, and removed all my folders in iTunes on my Mac and now it's working normally for the most part. I have to hit Download All a few times on my iPhone, but everything does download without having to touch each eternally spinning red circle. Not sure if this will work for others, but wanted to post.

The above solution has worked for me too! I've submitted a bug report.