Many online learners are facing challenges despite the reported growth in enrollment, and research shows that self-discipline and management of learning activities are key characteristics to succeed. The ability to self-direct learning activities can lead to improved learning experiences. In an effort to improve self-directed learning, various open source applications are evaluated for their functional attributes and capabilities. The applications being assessed include a course management system, wiki, and weblog. The goals of this study are to identify a set of open source applications that are suitable for a collaborative environment, and to evaluate the strengths and weaknesses of each application towards proactive learning. Based on the outcomes of this planned study, an assessment will be made as to how each application enables and facilitates self-directed learning activities. Additionally, a set of criteria will be established for empowering learners as self-directed individuals. Based on this study, instructors and administrators can be better informed to make appropriate decisions amongst the many open source applications available for learners.