This study explores the web-navigation practices of adult learners in higher education and re-conceptualizes the concept of the organizing circumstance of self-managed learning, originated by Spear and Mocker (1984). The theoretical framework draws on funds of knowledge theory from a cultural historical perspective and elaborates a Vygotskian concepts of learning and development by introducing the notion of the distal object and the zone of distal development. The study employed a mixed methods design with an embedded multiple-case study involving half of the twelve participants using a new technology for self-managed learning called Zonebee. Zonebee recorded participants' web navigation, known as Zonebee Trails, providing quantitative data for analysis. Surveys were administered, namely the Metacognitive Awareness Inventory (Schraw & Dennison, 1994), the Index of Learning Styles Inventory (Soloman & Felder, 1986), a survey of technology use (created for this study) and a set of demographic questions. Eleven of the twelve participants also provided interviews in which they described their self-managed learning practices. Findings contradicted the premise in the literature that the learning environment fortuitously determines the learning experience. Participants primarily relied on the internet and computer to manage their learning and made deliberate choices about which tools to use depending upon the purpose of the constituent process of self-managed learning in which they were engaged (assessing, planning, implementing, monitoring, evaluating or producing). Zonebee Trails evidenced participants' engagement in considerable planning before generating focused queries to locate specific materials. Thus, this study suggests that the organizing circumstance operates, not through happenstance alone, but through the confluence of four factors influencing the direction the learner takes: funds of knowledge for learning; learning demands (proximity of the learning object, proximal or distal), conditions for learning (affordances for and constraints on learning); and motivation or purpose of activity. The re-conceptualized organizing circumstance of learning, then, offers a methodological and theoretical way to redefine context and understand how learners manage their own learning. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]