BoxCutter - Can't Cut Shape All The Way Through

Hello,

I’m fairly new to the Box Cutter add-on and I’m confused as to why I can’t cut a shape out from the mesh that I have. In the photo attached, I’m trying to cut the cylinder out from the block from the front to the back. If I move the cutter back so that it doesn’t intersect both the front and back, it works fine (mostly) but I can’t figure out how to cut the entire cylinder out from the block.