A system for packaging one or more items includes an order arrangement station where the one or more items can be arranged into a stack with a desired configuration. A dimensioning mechanism determines the outer dimensions of the stack and a converting assembly creates a box template that when erected forms a box that is custom sized to the dimensions of the stack. A crowder assembly holds and maintains the stack in the desired configuration while the box template is at least partially folded around the stack. The box template is secured around the stack in the form of a box.