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@TeeTee
I have NOS 50s cotter pins too, and, yes, they're a lot higher quality than modern ones. Guys I've spoken to in bike shops say the same thing.
I've got the pins in the right way round - flat, wedge side facing the notch on the axle - but I can only put them in so both nuts are facing the same way, as the holes in the cranks seem to be slightly tapered (i.e. it's only possible to push the pin in from one direction). I wouldn't have thought that would make much difference, would it?
This is the first time I've tried these pins, but when I got the bike it had the same problem. I just assumed it was because an old cotter pin had been mashed up. I've got some cheap modern pins, so maybe I'll trial filing or something with them and see where I get.