I just went to tighten the adjustable cup on my 1976 Raleigh Gran Sport (a pretty new build, had maybe 150 miles on the cleaned, greased, and re-balled bottom bracket, and it had worked a little bit loose) and found that the green Park pin spanner I have won't quite fit. That is, I can get either pin to engage the holes in the cup, but not both together--there's just not quite enough clearance between the cup and the crank arm.
The crank was used when I got hold of it, and my guess is that this has happened because the crank is old enough and has been removed and replaced enough times that the square taper has "stretched" a little, so the crank bolt forces it little further onto the spindle than it did when it was new. The tapers themselves are in excellent shape--not rounded off of misshapen in any way. I also suspect that there's no way around this problem other than the obvious--pull the arm on that side, adjust the cup, then replace the arm. That's not the end of the world, but does anyone know some elegant way to adjust the cup without removing the crankarm?