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Changing strings on an acoustic

So I was changing the strings on my Michael Kelly Firefly, the G string changed without a problem, but the little stopper in the bridge (idk the technical term) will not stay in the bridge when I tighten the string, thus popping the string out. What am I doing wrong?
 
That would be the "bridge pin". If the ball end of the string is too far down into the bass when you push the pin in, it will catch on the tip of the pin and pull it out when you try to tighten up the string. Make sure you pull the ball end up so it's just below the top, so when you push the bridge pin in the tip clears the ball end when it's all the way in.

Mike