I'm trying to restring my acoutic, and the bridge pin continues to pop out. Wtf am I doing wrong. This is on the low E string as well. I don't know about the other strings yet.
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Insert the bridge pin with the string going through the string channel. Pull on the string to make sure the little wheel comes right up against the inside of the soundboard. Then push the bridge pin into the hole as far as you can, carefully. Tune the string to pitch.

If the bridge pin still pops out, you can use a small rubber mallet to gently hammer it deeper into the bridge. However, you need to put your hand inside the soundbox and support the underside of the bridge when you are hammering. This will also give you a chance to make sure that the wheel is right up against the inside of the soundboard.

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Zoom in on step three. That's what needs to happen. Though you obviously can't see it, it gives you an idea of what you're feeling for. There should be no pull on the bridge pin from the string itself. The string should be pulling up on the top of the guitar, the tuning peg merely keeps it pushing where it is. You probably have the ball of the string directly underneath or wedged in the tuning peg so when tension is put on it, it attempts to pull the peg out.

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I had the same problem not to long ago. Just do what these guys said. I had trouble when I tried to fix mine and had to take all the strings off so i could get my hand inside to make sure the ball of the string stayed off of the end of the tuning peg while i pulled on the string. I also invested in a bridge pin puller so I didnt damage my pins or my guitar when i tried to pull them out.
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