Cloth Simulation and Object Collision not working as expected

Hey all,

I’m relatively new to Blender, probably been fiddling around with it for a couple of months now, working things out as I go and reading/watching tutorials for what I need.

Anyway, this little project I’m working on I thought would be pretty simple, however I’ve run into some issues with the cloth simulation.

IDEA: Troll (imported model from elsewhere) Cuts through a flag/banner (Boolean Modify/Cloth Simulation), and walks through it (Object collision, also possibly wind from behind)

Problems:

  1. His head pokes through the cloth before the collisions take place.

  2. Once the collision finally take effect, the cloth becomes really distorted around his head.

  3. Baking the cloth simulation returns an evern worse result.

Pictures for the problems I’m having

Things I have tried:

  1. Merge By Distance on all meshes
  2. Numerous different cloth sim settings. It seems worse when self-collision is turned on
  3. Numerous collision settings on the troll.

If anyone has any suggestions for what I can do to fix this, that would be great. I’ve been pulling my hair out for the past couple of days.

Here is a stripped back version of the .blend file (Poses/Background Scenes/Extra Objects removed)

TIA for any help.