Why can't I play music from my speaker?

I am trying to fix my friends iPod 3G.
Here is a breakdown of the problem. And I'm not sure when he started having this problem. It may, or may not, have anything todo with updating to ios 5.0.
So, going to 'clock' and setting an alarm, the speaker works fine. Even when the alarm goes off when the time is right.
Occasionally the unlock gesture will produce a sound from the internal speaker.
When pushing the volume keys nothing appears onscreen. But, when headphones are present all sounds are made through them, and the volume keys bring up the onscreen feedback guage that also says 'Headphones'.
I have plugged the iPod into a stereo with a dock, and unplugged it while it was playing. That causes an otherwise unpresent volume slider to come up. And if I press play while the slider is still on the screen, music will play. But for only about 2 seconds, and then the slider dissapears and the music pauses. Leaving me unable to restart it unless I plug it back into the dock, or insert headphones.
Seems to me to be a software issue rather than hardware.
I've tried holding the volume keys, and plugging/un-plugging headphones repeatedly, as these were cited as potential fixes.
I have restored the device in several different ways. And I have now just jailbroken it for the first time. Seemingly the unlock gesture sound is happening more often than it did, but it's still not consistent.
From what I have read this is a common problem, with no real clear solution. But to me the problem seems pretty straight forward, if you can get past that it has nothing to do with the volume buttons....
Thanks for your potential insight.

Welcome to the Apple Community.
When you say you can't play through both devices at the same time, what happens when you try, are you able to select multiple speakers, do they deselect themselves, do you not get the option or does it just not work when you select multiple speakers.

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