Trying to understand cloth/capsule collision

I have a large piece of cloth that is set up to interact with one capsule collider -- sometimes the capsule appears to go through the cloth, sometimes it stops at the cloth and others it stops before it even gets to what appears to be the cloth (but actually is ~ the perpendicular to the front of the cloth piece)

To try to understand this, I turned off gravity so the cloth floats more freely and turned off the rendering of the capsule mesh. In the image you can see that the collider won't proceed beyond the perpendicular of the frontmost piece of the cloth.

Is this expected? I there a way to make the collision more closely track the visual representation of the cloth?