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Hey Brett, try following the instructions here to make sure you're doing it right.
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rekordbox newbie
Hello all,
newbie with Rekorbox and I have made several attempts to import itunes and all times have failed. I can see my library tree and playlist but downloaded music still shows not DL and some playlists just show blank with no songs. I have turned on my xml integration / sync - reloaded RB twice. please help
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Please check the file formats of the files to be imported. Even files with content protection from iTunes are not compatible with rekordbox.
I am not using this functionality, but this may be a starting point to start your investigation.
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