Technological tools continue to permeate modern life, to the extent that they can supplant previously fundamental skills. Maps and route-finding are no exception. This complex function, driven by huge volumes of data, makes modern transportation easier, more resilient, and at the same time riskier and more dependent on a sometimes-opaque technology and revenue model. This case study explores a variety of instances of online mapping and route-finding, and invites the student to consider how these routes are identified and influenced.