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Im gonna go measure ring depth and the rings themselves. I have Manley pistons and these TS rings are what they stipulate because of the ring depth. I also have the single set of Mahles to compare to. I was thinking about using a tie wrap around the base of the compressor next lol! I agree about it being to tight, but the current situation calls for it to be REAL tight or im screwed.
I understand your situation. Sounds all too familiar. With the Diamond pistons, the compression ring grooves were not deep enough too, and the rings would not compress enough to get in the cylinder. I had file fitted the rings in the bores and knew that they were not end butting. With the too long oil ring expander, the oil rings would not compress without the expander ends overlapping. I suspect you are having a similar problem, although it could be the ring causing your problems. Good luck!! When you find the culprit, they will go in as easy as what you are accustomed to. 
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