A system, and associated components and methodology, that provides for automatic determination and supply of an amount of dunnage to fill the void left in a container in which one or more objects have been placed. The system comprises a dunnage dispenser which is operable to dispense a controlled amount of a dunnage, a container scanner, and a logic device. The container scanner includes a height sensor for sensing a height characteristic of a container, a width sensor for sensing a width characteristic of the container, and a contour sensor for sensing a contour characteristic of the objects in the container. The logic device can (1) process sensed characteristic information from the height sensor, width sensor and contour sensor, (2) determine the amount of dunnage needed to fill the void not occupied by the objects, and (3) command the dunnage dispenser to dispense the determined amount of dunnage.