Discussions of online education often center on pervasive media, which allow for immersive and distributed education. However, when the curriculum is explicitly designed to train students in the expert use of software and systems for web cartography, how might educators best realize these opportunities in online education? We discuss two challenges: 1.) how to teach distance learners a technologically-demanding, yet cartographically-focused curriculum, and 2.) how to design and implement this curriculum within a quickly shifting landscape of workforce needs? We overview efforts to support a new generation of cartographers, enhanced with the technical capacities of open web standards, source coding libraries, and Git-enabled distributed version-control systems.