History feature not working

Hello, I am trying to figure why the history feature is no longer working for me. I am using a Patriot USB  stick and I used to be able to play different tracks, then take the USB out and when I put it in my Mac and open up rekordbox I could find what I played before. Now when I am open it it shows the same histories but none of the new stuff I had been playing. My settings look fine and they have been applied to the USBs. Can someone shed some light. I couldn't find much of a resolution in past posts. Help is appreciated.

Thanks