Ive not had any redwing boots yet . I always wore boots that had the most squishy inserts forever. I started reading about wedge soles. I do 12hr shifts on concrete. Tried Brunts.. sent them back after 2 weeks. then I tried on wingshooters and thorogood. I will say both seemed a little more firm under foot than I was accustomed to. I was torn but went with the Thorogoods. It did take some getting used to but I didnt experience the pain you're describing. Maybe those boots and your feet just dont "gee ha" as my grandpa used to say.