I've been having problems with a Winchester hiwall 32-40, the link that's also the firing pin retractor, acts as an interrupter. When I have a tight case, the block goes up, but doesn't drop down as it should, and then the firing pin retractor won't let the firing pin go all the way in to bust the primer. It's a royal pain in the ass! Has anyone else had that problem?

The barrel tenon may be too long, the rim recess too shallow, or a combination of the two. 
.005 clearance from case head to BB face with the case seated will allow proper movement and drop.
The reduced diameter at the end of the tenon may be too large, the step may be too short, or it may have too large a radius at the transtion.

I need to explain further, what has been happening with this rifle while shooting a match, it would occasionally misfire for no apparent reason. At first, I suspected the firing pin, or possibly that it was hanging up on the hammer fly. I ended up replacing a few worn parts, but the misfires continued, and so, by process of elimination I knew it had to be the firing pin retractor. What was happening was that I’d be shooting it in a match, breech-seating bullets and shooting some nice groups, but then it would start misfiring. If I just recocked the hammer and shot, I’d get a terrible shot. This is the sort of thing that will make you crazy! It turned out that what was causing this was that I slightly bell the mouths of my cases so that they will seal, but if the case is a bit too tight, the block will not drop down properly and will cause a misfire. The way I’ve remedied this is that when it misfires, I drop the lever down and close the action again, and then it will usually fire properly and I’ll get a good shot. I can’t be the only one whose had this problem.

I never had this with any 'wall I have owned, but seems to me that a gun with extra headspace might let the 'fin' on the firing pin come into contact with the  nub on the link and prevent the primer from going boom. Deep seated primers might even do the same. Maybe I haven't thought this thru enough, but it may not be a bad thing to check your headspace.