A method for producing a pair of boxes in parallel within a single source of packaging material at an electronic packaging system, the electronic packaging system having packaging system characteristics, the electronic packaging system including multiple packaging production machines, each packaging production machine having packaging machine characteristics, each packaging production machine loaded with packaging material for producing boxes, the method comprising: accessing item data identifying a plurality of items that are to be packaged; determining packaging requirements for each of the plurality of items; selecting a pair of box sizes for parallel production within the single source of packaging material at a packaging production machine, the pair of box sizes including a first box size for packaging a first one or more items in the plurality of items and including a second box size for packaging a second one or more items in the plurality of items, the pair of box sizes satisfying the packaging requirements for the first one or more items and the second one or more items, wherein the first box size is different from the second box size; selecting the packaging production machine from among the multiple packaging production machines, wherein selecting the packaging production machine takes into consideration at least the current and future workloads of the packaging production machine, the cost of operating the machine, and the size of source material available at the machine comprising dimensions capable of producing the pair of boxes in parallel; generating box production instructions in response to the selection, the box production instructions indicating how to produce in parallel a box of the first box size with a box of the second box size at the packaging production machine; and sending the box production instructions to the packaging production machine. accessing item data identifying a plurality of items that are to be packaged; determining packaging requirements for each of the plurality of items; selecting a pair of box sizes for parallel production within the single source of packaging material at a packaging production machine, the pair of box sizes including a first box size for packaging a first one or more items in the plurality of items and including a second box size for packaging a second one or more items in the plurality of items, the pair of box sizes satisfying the packaging requirements for the first one or more items and the second one or more items, wherein the first box size is different from the second box size; selecting the packaging production machine from among the multiple packaging production machines, wherein selecting the packaging production machine takes into consideration at least the current and future workloads of the packaging production machine, the cost of operating the machine, and the size of source material available at the machine comprising dimensions capable of producing the pair of boxes in parallel; generating box production instructions in response to the selection, the box production instructions indicating how to produce in parallel a box of the first box size with a box of the second box size at the packaging production machine; and sending the box production instructions to the packaging production machine.