Twenty-first century higher education instructors are continually tasked to review, align, pilot, adopt, infuse, and evaluate new tools and resources into curricula rich with standards regardless of course format (online/ distance, hybrid, and face-to-face courses). Demands often overwhelm instructors who cannot assume that all students approach technology with the same levels of expertise. Before courses begin, instructors should pilot these tools and applications to determine accessibility, types of support students may need, as well as determine what types of digital footprints students will leave behind. Digital footprints are unique data trails Internet users leave behind intentionally or unintentionally. Communicating expertise regarding digital footprints is imperative; information shared via the Internet (even when deleted) is never retractable--thus creating implications for students enrolled in school as well as graduates searching for employment. This article discusses digital footprints, implications for online learning environments, and generating active digital footprints to gain/maintain employment.