It is possible that you have not gotten the plug down to the last set of interrupted threads? I don't own one but have handled them a few times, but if I remember correctly it will not close period if the last set of threads are not engaged. The plug does have an "UP" and a small stem that would prevent you from installing it upside down. Could it be that the extractor is jamming in the channel?
The first time I looked at one the gunsmith removed the plug and re-installed it, but didn't get it down to the last set of threads. The extractor was jamming on the notch and would not close without a primer, so that may not be your problem.
What type of primer are you using? They are not all the same dimensionally, especially the length. Maybe try a different brand of primer.
Make sure the plug is completely tight, the O-Ring does cause a bit of resistance.