Problem:
I think I have found a solution to the problem, not exactly nice but it works.. I attach my Bold to my home stereo using the 3.5 MM jack to RCA and it never detects that I'm connected to headphones jack. So you unplug re-plug 10-20 times and eventually it detects it and pipes music out the headphone jack.

Solution:
I found that after you plug your headphone jack in (make sure its all the way in) if you take the extruding part of the connector and pry up slightly so the tip is forced down toward the back of the Bold (do it very gently and don't use a lot of force) it will detect that the ear phone is connected.

It works every time for me now, even my external speakers at work did the same and now works 100% when I do that.

My 2 Cents:
Seems to me that a connector inside the jack just doesn't protrude our far enough and you need to do that to get it to make contact. I'm wondering though by doing this if I am making the problem worse down the road or making the connector looser from the internal board.

Let me know if this works for you or not.

Sounds like your Bold is defective, get a new one.

I got mine from a friend at RIM not going to return it. If that's the worst thats wrong with it then I'm fine. I use headphones that I got at Future Shop and they work 100% of the time. So why they work and not ones that connect to my stereo I'm not sure.

Wirelessly posted (8700c)

Try a new rca to stero connector maybe? Could be that the one youce got the stereo connector is made rather small which would account for you having to fiddle with it each time.

Who knows for sure if it's too small or the hole to to large.... were still talking about BBs right?? okay just checking but it seems to fix the problem and just wanted to know if it works on anyone else's Bold that has this problem.