iPod sync process gets disrupted/need to restore

I’ve had this issue several times now. I recently upgraded my iPod classic to a bigger hard drive. After updating to Catalina, it seems like my iPod has had a difficult time syncing (although, my music library has also grown). It seems that my iPod will regularly forget my music library and I have to restore it once a week. Anyone having a similar problem or know a solution?

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Answer this question I have this problem too

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