Abstract: Systems and methods are disclosed for handling items for custom-sized multi-item packages. In one embodiment, an example system may include a multi-item loading component configured to support multiple items, the multi-item loading component including a first surface, a second surface disposed at an angle with respect to the first surface, a first sidewall configured to slide in a vertical direction from a raised position to a lowered position, and a second sidewall configured to slide in the vertical direction from the raised position to the lowered position. The system may include a pusher component configured to push the plurality of items off the multi-item loading component when the first sidewall and the second sidewall are in the lowered position.