Abstract: A system, method and software program for transmitting a digital image from a first communication device to a second communication device at a digital image service provider over a communication network. An upload software computer program dynamically analyzes certain properties of the first communication device and of the communication network connection with respect to predetermined criteria, and based on the analysis determines a strategy based on predetermined criteria for transmission of the digital images. For example, the upload software determines the number of communication threads and divides the digital images into a plurality of individual data packets each having a unique ID. The receiving communication device verifies receipt and determines if all of the plurality of individual data packets have been received and requests failed packets be resent.