How fast are you turning the 33/64 drill bit? Somewhere in the 450 RPM range (~60FPM) would be about right for annealed O1, maybe a bit slower would be helpful, and don't baby it, if you let the drill rub it will work harden the work instantly. My preference is cobalt bits for working with tool steels. Sounds like you need a counterbore tool bit. If you don't have a set, you should get some. I have 2 sets, one set with onsize pilots and the other with clearance hole size pilots. Turn them at about 1/2 drill speed or less.
https://www.amazon.com/s?k=counterbo...ref=nb_sb_noss