Hybrid file delivery systems and methods divide one or more files into parts for transmission to plural user devices during a first transmission phase employing one or more one-to-many communication paths (e.g., broadcast or multicast), and then transmit missing file parts to designated user devices during a second transmission phase employing respective one-to-one communication paths. User devices are configured with specified criteria for when and how to report file delivery status to a file delivery center that maintains a database of target user devices, file delivery campaigns, and statuses of file delivery completion at the user devices. The file delivery center can employ the database information to determine cost benefit for delivery of a file using two different transmission modalities and control when to switchover to or commence the second transmission phase after the first transmission phase.