Yes I have encountered this with a audio book on USB.
While the recent played list shows the last track it will only play the last track, you have to navigate to the artist book subfolder and then select the track previous and then advance forward to enable the loop playing icon so it will advance to the next track.
This is especially a pain in the ass as there is still the bug where the car will sometimes decide it want's to listen to the audiobook in the middle of the night and advances two of three hours forward in the book.
There used to be a work around where the source selector had history for each source and you could select another source before leaving the car.
That functionality has now gone away!!!