Technologies for applying a redundancy encoding scheme to segmented portions of a data block include an endpoint computing device communicatively coupled to a destination computing device. The endpoint computing device is configured to divide a block of data into a plurality of data segments as a function of a transmit window size and a redundancy encoding scheme, and generate redundant data usable to reconstruct each of the plurality of data segments. The endpoint computing device is additionally configured to format a series of network packets that each includes a data segment of the plurality of data segments and generated redundant data for at least one other data segment of the plurality of data segments. Further, the endpoint computing device is configured to transport each of the series of network packets to a destination computing device. Other embodiments are described herein.