Should say my Tags are not updating correctly in title
I noticed recently when I was adding new tags under My Tags that when I synchronised my USB the tags were not updating correctly. I did a test on an entire playlist and tagged the whole list *tech*. I then reloaded the tags on the MP3s and restarted rekordbox before pressing sync with my USB. As you can see lots of the MP3s have not had the updated My Tag added. What am I doing wrong?
Here I have updated the playlist with Tech under my tag.

Here i've pressed sync and its exporting

Here's the resulting playlist on my usb with the tech tag missing from lots of the songs:

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Should say my Tags are not updating correctly in title
Were the tracks with the tags missing already on the USB drive before the export?
What about those with the tags? Were they newly exported or already on the drive?
All of the tracks were already exported and on the USB drive. I just updated the tags on rekordbox and then sync'd but not all of the tags were updated.
I am experiencing this same problem, I am on Rekordbox version 5.8.3 Rev 18101...
Not only did I loose all my Tag information after I updated to this latest version. I recovered by updating my collection from my USB. But now I noticed that if I go back into my Playlists and update the My Tag information it does not update the exported data on my USB. The only way to get the information truly updated is to remove the playlist from my USB, eject, then place the USB back in and since I have Sync Manager monitoring these playlists and USB combo the Playlist is automatically updated on the USB. Then finally it is there.
One more thing to add. I only experience this issue when I export my playlists to USB devices. My laptop has a built in SD Card reader and I also use SD Cards. This does not happen on the SD Cards.