6.5X55 always needs trimming - why?

I suspect that you are oversizing your brass. Your chamber is larger than the resized brass. Next time try turning your die out about 1 1/2 turns so you are only partially neck sizing it and see if it will chamber. If not gradually turn the die in until the brass will chamber and set your die there. If you reload your brass often the way you are doing it you may wind up with head separation. When you have to trim your brass this excess brass is coming from the case and it usually flows from the walls just above the web (about 3/8" above the base). You can feel for this with a bent wire or cut a case lengthwise and it will be evident.
 
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My guess is the FL die is touching the walls of the case when you try to neck with the FL die turned out a bit. This causes the base to buckle out, which is probably where it is hanging up....
 
It has been mentioned already but I think it needs repeating. If I have a cartridge/chamber problem, I take a felt pen to the cartridge. Where the chamber interferes with the proper chambering of the case, the felt pen will be rubbed off. This eliminates a lot of speculation as to the problem.
 
I'm just going to add in here that for me, pretty much all of the bottle neck calibers need trimming (for me). 6.5x55, 8mm mauser, 308 winchester (they can be the worst), .223 remington, .303 british, 7.62x54. Only the 7,62x39 doesn't seem to "stretch" too much. I used to just neck size a lot of those, but I started getting rounds that wouldn't chamber, so I went back to FL resizing, and just bought more brass. I notice it isn't as bad on second and third reloadings, but after the first shot, they stretch quite a bit.

Last night, my .308 was 2.029 and trim length is 2.005 that's a fair bit of bifference, and I don't reload "hot" loads.

As a last comment, winchester brass is the first to bulge and split, PPU and military brass is the best (harder to resize but lasts a lot longer). S&B resizes the best of all of them, but I think is a softer/thinner case as well (doesn't bulge very often though). I completely stay away from winchester brass, I just throw it away when I come across it.
 
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