Did you modify the cloth object after the simulation was assigned? Cloth doesn’t like certain modifications. You could try removing the cloth physics from the cloth object and re-creating them, it sometimes solves issues.
Make sure the normals on the obstacles aren’t inverted.
Make sure the “single sided” setting is active on the obstacle (it should be by default) and possibly try “override normals”. Those 2 settings can improve collisions.
Does any of the objects have modifiers on them that could modify their position or shape?
Ive tried redoing the cloth several times, so I dont think its got anything to do with a certain modification. Maybe the problem is in the grate, I’ll check.
Update: I tried every suggestion you gave and recalculating the grate’s normals seemed to fix the problem. Thanks!