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I turned 2 today. First was so hard to take off ihad totrim the end to get off. The second i made smaller design. having a hard time gripping it to remove. Why am i having such a hard time? The stopper is 3/8 i used a 5/16 drill bit and taped it wirh a 3/8 tap. Could ibe using too small a drill bit.
 

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Pictures would help.

Are you using a bottoming tap where the cutting threads go all the way to the end?

Cutting the threads with a tap is easy. If the hole is not deep enough so that a normal tap did not cut threads to a length the same as the stopper, I can imagine it to be difficult to get the stopper mounted.

I normally do not have a problem getting the the stopper into the threaded hole.

You could try 11/32in dia drill bit.
 

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try putting some wax on the mandrel threads. that should keep it from locking up. I don't use a threaded mandrel but here is my video on turning a bottle stopper. It was really a video done to show someone how to keep rubbing the bevel as you turn the top end of the stopper. My other video on turning a cove should help with the other design elements of a stopper.
 

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Two tips for ya. First back it off the mandrel after turning/ sanding but before applying finish. Easier to get off before finish is applied, usually. Next get a strap wrench for those really stuck ones, they're a life saver.
 
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