Replacing the Rack and Pinion and I cannot get the steering column back onto the input shaft for the rack

At first, I thought the input shaft might not have been long enough on the new part, so I measured it out and it's the same. I also tried to reinstall the old one, but I am having the exact same problem putting the original back in.

First, I tried while the rack was fully bolted up, but it wouldn't go on far enough.

Then I tried it while unbolted and I was able to get it on further but still not far enough to get the set bolt in.

I've been trying to twist and rotate for the last couple of weeks with zero progress. I haven't found anything online yet. Everything I see is basically saying it should just slide right on no problem. I'm hoping there is some kind of trick or step that I am missing.