How to prevent the cloth sim from breaking after changing the transform.parent of an ancestor

The question pretty much sums it up, but here's my setup in the hierarchy (-> means parent of):

Object1 -> Object2 -> Interactive Cloth / Cloth Renderer Object3

The cloth sim works fine until I modify either Object1.transform.parent or Object2.transform.parent (either setting to null or another transform). Once I do, the cloth sim breaks down. I see my cloth mesh 'crumple up' and it also detaches and falls to the ground without tearing off if any physics impulse happens (tearing off is disabled).

Is this a unity bug? Is this a limitation of the cloth sim? Anyone know what is going on here?