The field of education is experiencing a rapid shift as internet-enabled distance learning becomes more widespread. Often, traditional classroom teaching pedagogical techniques can be ill-suited to the online environment. While a traditional entry-level class might see a student attrition rate of 5-10%, the same teaching pedagogy in an online environment can experience dramatically higher student attrition. The CIS Department at Mount Olive College is addressing the challenge of technology/business applications literacy by implementing a new e-learning solution. A customized, self-paced, web-based 100-level tutorial using a novel approach in which students interact with an application’s embedded search and help features. This interactive learning activity encourages students to utilize the built-in “help” features to solve the problem or task at hand. As students become proficient at using these “help” features, their proficiency, confidence, and student engagement in the class material increases. The course online facilitator is able to shift their time and energy from “putting out fires” to focusing on higher-level feedback on assignments and administrative functions. Since more classes require the use of application software in completing assignments, students take this newly acquired problem solving approach to other situations and courses, enhancing their progress throughout their undergraduate program and increasing the probability of program completion.