Cranial Helmet but Side Sleeper? Does it hurt?

Hello this may be a stupid question but any parents that has/had to put cranial helmets on their side-sleeper baby, I was wondering if it pushes on their face and does it hurt with the pressure? We are on our third day and he is having such a hard time napping/sleeping with it on. He keeps moving to lay on his preferred side like he usually does and then cries. He is almost 8 months old, crawling, pulling up to stand, and of course rolling both ways.