Quoted: Try wiggling it in a circular motion while pushing on it...
You could also put the blade of a small flat screw driver in the cotter pins slot near the head and then squeeze the end that goes into the carrier with a pair of jewellers pliers... That will close the gap and allow it to find the hole easier... You could use regular pliers too if the teeth on the jaws are covered with tape... Be careful not to chew it up with tooling marks or it will be harder yet to get back in...
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On the Olys I have I put the pin in the first hole, push against the other where it is hanging up, then I use a Dental pic to compress the side of the pin hitting and it slides in. Why it does that with Oys? I'll guess, since I have never compared it to the other Colt, CMT, LMT, and Armalite bolts that I own, that the hole is chamfered in there on the spec' bolt carriers and not on the Olys.
That may not be the case, but it sure seems that way, and theirs are the only BCGs I have run into that does that. I have also wondered, but never tried it yet, as to whether a KNS Perma-Pin would slide in there the way the regular pin is supposed to. Have any of you guys tried that yet on OLY carriers?