Yes
I have a 2013 limited with the same issue and any time USB is used and explorer is restarted it defaults back to the first song
I was told nothing can be done at this time to correct
I do not have this problem. I use my USB stick all the time and the only time it starts over is when it does the random re-indexes.
Sounds like your USB flash drive is reindexing every time you start the car.
To reduce how often that happens, try:
1.) put all your files in a flat file structure - no seperate folders for songs/artists/etc...
2.) trim all the file names to remove special characters, spaces, etc.... The shorter the file name the better.
3.) Download a tag editor and remove all information from the MP3 tag EXCEPT Artist, Song Title, Album, Genre, and Cover Art.
Step #3 is actually pretty important. For some reason, Sync doesn't like certain tag fields. Especially the compilation check box. Make sure that is unchecked.
The other thing that can happen is that it seems that sometimes Sync never actually properly creates the index upon startup. For some reason the index created upon start up appears corrupted so it will reindex everytime you start the car. To fix this, once Sync is done building the corrupt index, have it rebuild the index manually. There is an option to do this.
Note that these procedures substantially reduce how often this happens, but sometimes it just happens.
Finally,
to speed up indexing, pause playback from the USB device - this works wonders on improving speed as the system isn't accessing the USB interface for two seperate tasks - I have 750 songs on my USB drive and it takes about 1 minute max (I've timed it) to index
