I'm in the process of building out my long block and have hit a roadblock while installing the pulley.  I can get it on just short of where the stock retaining bolt will grab the crank nose.  I've been using two longer bolts to draw the pulley onto the shaft.  I've pulled the pulley off and inspected the keyway and the bore.  There is a bit of a lip - just detectable with my dental pick - about 1/3 of the way from the nose of the pulley.  The nose end has the larger diameter.  I've cleaned and inspected the keyway.  A loose woodruff key goes on about 1/3 of the way from the nose - about equal with the ridge on the bore - and binds up.  I've tried both the used key that came out of it and a new one - both with the same binding issues.  The engine shop didn't indicate the crank has been changed out.  The pulley stayed home.  BTW - It was a breeze when I took it apart 3 months ago.  Pulley came right off - no struggles.
I don't want to hammer it on and was reluctant to use a lubricant such as WD-40.  Nor did I want to dress the side of the woodruff key.  One thought I just had is to lightly dress the side of the keyway with an ultra-fine file just to see if there is a burr or spot of rust I haven't found.  It won't take much to bind stuff up.
For fear of really screwing things up, I was reluctant to go much further without some input as to acceptable courses of action or other things to consider.  What are your thoughts?

Just to be clear to me, you’re talking about the installation of the dampener, right? Car, truck, ‘bird?

miker
55 bird, 32 cabrio F code
Kent, WA
Tucson, AZ

Yes - dampener in a car.  272.

How about removing the key. Then try fitting the damper without key in place. This will tell you if problem is the key fitment or damper diameter which may be the problem area. Do you have the old damper to compare internal diameter sizes.
All the best
Phil NZ

Good idea.  Isolates/eliminates a potential problem area.  In thinking about it, there are only two areas where it could be binding up - the bore or the keyway.
The dampener is original - came off the (presumably) same crank about 3-4 months ago.
My plan today is to remove the dampener.  I'll then check the fit without the key in place.   If it doesn't go on, I'll check the bore of the dampener - maybe run some steel wool through it just to clean it up.  Then make sure there aren't any burrs, rust spots, dirt, etc in the dampener keyway making sure the key slides the entire length of the sleeve. 
Thanks for the input.
Mike

I've used Emery cloth on the crank and inside the pulley to some success. It sounds like the ridge is your problem area. Just try to smooth that a bit. Sometimes a few taps with a rubber hammer will do it. Only in the center though. When I set up my blower adapter I was able to get a longer center bolt from the local nut and bolt shop.

Y's guys rule!
Looking for McCullouch VS57 brackets and parts. Also looking for 28 Chrysler series 72 parts. And early Hemi parts.

MoonShadow, 292 w/McCulloch, 28 Chrysler Roadster, 354 Hemi)
Manchester, New Hampshire

272 & 292 crankshafts are the same. If your dampener/pulley was designed for either, it shouldn't be a problem. However, I've seen photos of broken crank snouts caused by trying to hammer on the dampener. Although it isn't cheap ($59.95), you can get the correct installation tool from either Casco or Hill's Thunderbird. 

When I sent my 55 Tbird dampener to Damper Dudes to be rebuilt, they said that mine was in pretty good shape, better than most that they receive, which are pretty beat-up from hammering them off. I don't like spending money on tools that are seldom used (maybe only once), but having the correct tools makes the job easier and can save you money in the long run. 

Assuming your dampener was rebuilt, was a sleeve installed over the snout? Although I'm sure that the groove cut into the snout of my crankshaft from rubbing against the timing-cover seal was shallow enough to be polished out, Damper Dudes installed the sleeve over the snout. Maybe you're experiencing interference between the snout and the timing-cover seal.

Yes, the damper was rebuilt and a new wear sheeve installed but was hanging up before it engaged anything.
Success.  As suggested by Phil - I tried putting the damper on without the key in place.  Didn't go on/ hung up at the same place, so that led to the next steps.
Took a cylinder hone that was slightly smaller diameter than the damper and gently made 3-4 passes just enough to clean things up.
Took a flat tile and made a few passes on the sides of the keyway until the loose key would slide thru without binding up.  I think I had a burr or rust spot.
Chamfered the flat corners of the key slightly just because I could.
Finally, I went old school and read the shop manual.  They said to coat the crank nose with a mixture of white lead and oil and to pound it home with a soft metal hammer.  I was all out of white lead, so I used white lithium grease and drew the damper home using longer bolts, spacers, etc.
Thanks for your input
Mike