Handling systems and methods for reorienting inventory items

An orienting apparatus configured to reorient an inventory item supplied to a packaging machine includes an inlet, an outlet having an aspect ratio less than one, a translation device, a vertically oriented guide, and an orienting guide. The translation guide drives the inventory item from the inlet towards the outlet. The vertically oriented guide is positioned between a first lateral side of the inlet and a first lateral side of the outlet. The orienting guide is positioned between a second lateral side of the inlet and a second lateral side the outlet. The vertically oriented guide and the orienting guide define a channel through which the inventory item is conveyed. The orienting guide interfaces with the inventory item to progressively reorient the inventory item as the inventory item is conveyed through the channel.