As educators and administrators look to countless mobile apps, software programs, and web-based learning tools to meet the demands of students in remote, virtual, and hybrid settings, risks and assumptions of online platforms and assessments must be considered. With the urgency of the COVID-response closure of many schools and the unusual methods employed during the return to school in Fall 2020, there is no better time to examine the digital application literacy which is necessary for students to effectively transition to online learning and assessment. "Digital application literacy" (DAppLit), a specific form of media literacy, involves the nimble use of an app (web-based) or application (computer-based) for education, including assessment. Learners with impaired DAppLit face academic consequences, when insufficient literacy in the platform is the culprit. This paper first explores various skills and strategies from both traditional and digital assessments that digital application literacy requires. Then, it presents the value of low-stakes assessment experiences with applications to introduce navigation techniques and troubleshoot barriers users may face before undertaking weighted assessments. The importance of skills instruction and practice of DAppLit methods is presented. A four-step process is introduced to: (1) set learning goals; (2) guide learners through the application with explicit instructions before use; (3) provide low-stakes explorations; and (4) debrief to address any issues which could represent a failing of application literacy and not content knowledge in an assessment.