I have only ever owned three sets of Redding dies and two have given me fits.
I just bought a set of Redding 375 H-H dies. When I go to run the new brass the case goes in just fine and easy like it should but when it comes out it is like the expander button is going to rip the neck off.
I have a set of 270 win dies that did the same thing. With the 270 dies I just took the button out of it and replaced it with a 22 cal button.
The Redding die set that I love is a deluxe set with the neck sizer and FL sizer in 300 WSM. I have had zero problems with that set.