I ended up fixing it and wanted to post here in case someone finds this thread in the future.
When I moved the die to my turret press, I grabbed the directions to make sure I had it set up right as it has been probably six or seven years since I set it up and haven't moved it since. I mistakenly grabbed the directions that came with the Lee .243 dies, not the 30-06 dies. The .243 die is set by running the ram up and screwing the die until it contacts the shell holder. On the 30-06 dies, you have a case in the shell holder and screw the die down until it touches the case mouth.
I had the die screwed in way too far and the crimp feature was crushing the case. I set it up right and am back in business.
It seems strange to me that some are different than others within the Lee line, but I looked at the directions side by side for 10 minutes and it's clear as day.
Anyway, I'm back in business.
