An electronic shipping container labeling system for labeling a plurality of shipping containers transported through a shipping system. The system includes a plurality of electronic-ink shipping labels affixed to a plurality of shipping containers. Each electronic-ink shipping label displays graphical indicia representative of information relating to the status of the shipping container within the shipping system. One or more activation modules are provided throughout the shipping system for transmitting electromagnetic data signals to electronic-ink shipping labels and providing instructions to updateable electronic-ink shipping labels employed in the determination of graphic indicia to be displayed on electronic-ink shipping labels. Each electronic-ink shipping label employs an addressable display assembly including a layer of electronic ink including a bi-stable non-volatile imaging material. The electronic-ink shipping label includes an integrated circuit structure having a storage element for storing instructions, programs and data, and a programmed processor in communication with storage element. A signal receiving structure receives electromagnetic signals from the activation module, using the antenna structure. The electronic-ink shipping label displays graphical indicia representing information relating to the shipping container and/or its contents.