A large container loading system and method for a packaging machine includes an infeed conveyor and a transfer flight. An array of pivotable cradle lugs is carried by the transfer flight in synchronized movement with cartons on an adjacent carton flight. Containers are moved into the cradle lugs in an upright orientation and the cradle lugs and containers are reoriented to a substantially horizontal or sideways orientation before being pushed into their cartons by an inserter assembly. A transfer block or a support conveyor may be positioned between each of the cradle lugs and an aligned open container to support a container as it moves between a cradle lug and a carton.