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Not all playlist songs transferring from Wear app to Gear S3 Frontier

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I've had my Gear S3 Frontier for over a year and a half now and I've been building up a playlist over that time on my phone (Galaxy S7 Edge) and transferring the playlist to my watch through the Gear (Now Wear) app. I didn't notice this until recently but the watch only has about 80 of the tracks from the playlist when now the playlist has around 170 tracks on my phone.

I have deleted all tracks off my S3 and tried to transfer the whole playlist again but it still only transfers 80 tracks or so. I've checked the storage and it's not full so I don't think that running low on storage is the problem.

 

Can you guys help? Is there a max number of tracks that the S3 can store?

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