It is not possible to play duplicates of a file.  In the example below, avi.avi is played correctly the first time, but the second and third time, pressing play will simply skip them. This behavior only affects files with the same name. If a file as a different name, the media player will have the expected behavior for it and for the next time that the "original" file is played.

Only the first avi.avi and the very last avi.avi of the list is being played correctly.

After testing, it seems that the subsequent avi.avi are in fact being played. The issue is that the media player seems to register the file as finished playing and is keeping this "timestamp" for the next video being played. This cause issues when the same file is used multiple time.

When playing the second and third avi.avi, no video is displayed, but you can hear maybe 0.1 seconds of the end of the video.*

This behavior is only observable when a video finished to play. It doe not manifest if the "next" button is pressed.**

This behavior is also observable if you press "previous media" and try to play it. Only the very end of the media will be played (0.1 second).***