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The purpose of this exploratory and phenomenological study was to investigate how nontraditional males who dropped out of a western four-year, Title IV authorized, public university before completing a bachelor’s degree described their perceptions of their situation, self, support, and strategies while moving in, moving through, and moving out of the college process. Fourteen interviews were conducted in person. Participants met the following criteria: (a) only included males; (b) met four or more nontraditional criteria to be included in the study; (c) were enrolled in an undergraduate degree program; (d) were enrolled within the last two calendar years with the intention of earning a bachelor’s degree; and, (e) dropped out before obtaining bachelor’s degree. Interview questions were divided into three categories based on Schlossberg’s Transition Theory: moving in, moving through, and moving out, with four areas covered in each category: situation, support, self, and strategies. There were eight recurring themes—personal and institutional related. The personal themes were: (a) participants appeared to be family oriented; (b) a perception of time issues/constraints; (c) job related issues/constraints; and, (d) financial concerns. The institutional related themes were: (a) perception of institutional support; (b) faculty interaction; (c) a perception of lack of follow up from the institution when participants did not return; and, (d) a lack of understanding of what is expected when a person attends college (unknown expectations).