[samuel1613]

The media player continues playing regardless.

Here's exactly what I do.

Start media player, put a few songs in the playlist, start it playing (I can hear it through the rear "speakerphone" speaker.
Plug in the attachment, speaker goes silent.
Plug in headphones. Nothing through headphones. (Other headphones, same thing.)
Sloooowly plug headphones into attachment, and jostle them, suddenly music starts coming out through headphones.
Song ends, next one starts, headphones no longer have sound coming out.
Repeat plug/jostle process, headphones start working again.
Rinse & repeat at every song.

It's just wierd, it seems the player loses the fact that headphones are plugged in at every new song. It's gotta be a software glitch or setting of some type because it happens at every new song, immediately when a new song starts, every time!