I'm talking about the last encounter with Chris outside, when you run towards him before ducking to your right and crawling through a hole in the wall. I've done this part over and over in practice but at this point it seems 50-50 whether he grabs your leg and pulls you back as you crawl through the wall or not.

Any tips?

I've found that if I take one hit or make him swing at least, then you can always get under. Not sure if its the quickest way though

I usually go towards him looking a bit the wall in the left and when I approach him I turn fast to the right. If you listen him complaining is that you did it right. There's a good example:
Anyway if you are not playing insane% you can always take a hit and do it safe.
Also we have a discord server where you can ask all this things and usually there's allways someone than can help you faster than here.
Hope I've been helpful. GL!

Chris has got a VERY long hit cooldown of 3 seconds. So that's why you can take a hit on normal and then just go (even if you got pulled out of the hole without previous hit taken you can go straight back to it)

Hey, wanted to do an update on this thread since after checking the configs again, turns out the cooldown for Chris is actually 4 seconds. So, um, yeah, sorry for misinforming you.