A mobile image capture and processing system including a digital image capture and processing instrument for capturing digital images of shipping documents associated with shipments to be delivered to an intended destination over a Web-based shipping, tracking, and delivery information network, and automatically processing such images to read a 1D or 2D bar-coded shipment tracking number graphically represented therein, and automatically encode the shipment tracking number within the header of the digital image file and the name or title of the digital image file. A Web-based portable data transaction terminal (PDT) or a Web-based portable digital assistant (PDA) is used to receive digital image files from the digital image capture and processing instrument via a first wireless data communication link, and transmitting such digital image files to (i) an application server supported on said network, and (ii) from said application server to a human-operated data-keying station supported on said network, where the shipping information contained in said digital image files can be read by human operators, and manually entered into a database (RDBMS).