Vintage Thunderbird Club International

Here's another concept for keeping those @#&* square headed bolts seated in their slots when reassembling the 60's steering columns. It worked for me and it might be of help for you.

I used a dab of hot melt glue to temporarily fasten the bolt heads into their slots in the steering column tube. Admittedly, it took me three tries to get the bolts oriented precisely so that they would line up with the holes in the upper collar housing, but the whole process was only a few minutes and the assembly was back together. By its nature, the hot melt glue holds the bolt heads to the column only temporarily, but gives the bolts some flexibility to align them into the appropriate holes.

And, as they say, your mileage may vary.

Excellent
There can never be too much brainstorming on this particular headache.

I stuck my bolts in the collar and stuffed a piece of paper towel between the threads and the collar housing to push the square head slightly away from the hole that it goes into... and then put it together. When you pull the paper towel out it goes right in and then you tighten it down.

It worked twice on the first try.