A system and method of augmenting a delivery route. The method comprises receiving first location information from a first position device and receiving second location information from a second position device. The method further comprises storing the first and second location information in a memory structure and determining, based on at least one of the first and second information, a time and a location for each of a plurality of stops. The method also comprises reconciling the determined time and location of each of the plurality of stops with a stored route comprising a plurality of stored stops, the stored stops having a stored location and a stored time associated therewith and estimating a plurality of transition times between pairs of the plurality of stops. The method further also comprises constructing an updated timeline based on the plurality of stored stops, the plurality of determined stops, and the plurality of transition times and updating the delivery route based on the constructed timeline.