I really am unsure what to call this issue in a sentence so I will layout what is going on as best as I can.
This used to happen occasionally, but now it happens every time I try to sync. I am using MC 28 on Windows 10 with an Astell & Kern SR25.
When I first run the sync operation and everything will work fine, all the music will sync properly and I'll see it on my handheld.
However, after this if I click the 'recheck sync' button, every song on the sync list that will say 'on device' after running the first sync is suddenly duplicated, but without any metadata (See images below, After first recheck sync pt.1 & pt.2)
If I try and recheck sync again, the songs with the metadata suddenly change from 'on device' to 'in queue' even though they are still all on my handheld (See image After second recheck sync)
Lastly, if I try and sync now all the 'in queue' tracks turn to 'error' and all the non-metadata tracks get duplicated (See images Attempting to run sync Pt.1 & Pt.2). Thankfully none of this alters what is on my handheld, but it makes managing syncing in JRiver impossible.
The only way I have found to reset all this is to delete everything off the handheld and sync it all again, but then the same thing as above just happens again.
This also makes any playlists I create on my handheld get deleted, since I have to remove all the tracks and re-sync them. So this all makes using JRiver to sync to my handheld impossible, and any help with this is greatly appreciated. Please let me know if there's any other information/settings I can share to help.