I’ve got the Enve 5.6 Disc wheels and wrote this: GP 5000 TL - fitting problems - #146 by bbarrera
your rims might be slightly bigger or smaller, and same with the tires, so your experience could be different.
and another thread I commented on Pirelli Cinturato Velo TLR as training tires: Best tubeless *hookless* tyres / tires - #10 by bbarrera
note: I ride on really crappy road and appear to be the Bermuda Triangle of flats and sidewall punctures.