I am dealing with a similar issue with an internal SSD. What is the drive formatted as? I have mine formatted as APFS and my waveforms are missing
Rekordbox - Sync new track on USB SSD Hard Disk
I explain my excitement in a few words
I have a very large collection on Rekordbox, more than 60,000 songs, I export it from Export Mode but not using Sync Manager all to my Silicon Power A55 SSD Hard Disk and everything works properly after about 8 hours of work.
When I go to add songs to a playlist and re-export it to the Hard Disk Rekordbox gives an error during the export and many files are not exported.
I don't know what to do anymore, this happens only on my two Hard Drives and not on the pen drives that have less files and can be solved only by formatting them. At that point re-exporting everything, with updated playlists it doesn't give errors.
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My SSD Hard Disk is Fat32 formatted
Guys I solved my problem thanks to a guy, I had playlists with more than 1,000 songs, and by dividing these playlists everything was solved.
I hope this can help someone else