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The phenomenon of encountering instrument meteorological conditions (IMC) on a visual flight rules (VFR) flight has been the focus of several previous studies. Most of these past studies, though, have involved examining various databases quantitatively or via a mixed-methods approach in search of possible causal factors such as pilot characteristics, weather conditions, aircraft type, and time of day. Missing from the literature are qualitative studies that tell the story of pilots who actually experienced such flights. To help fill this gap in the aviation literature, the purpose of the current study was to describe the first-hand experiences of GA pilots who inadvertently flew VFR-into-IMC. Participants consisted of 11 male pilots who previously had flown from VFR-into-IMC inadvertently at some point during their aviation career. The study used a phenomenological approach to describe participants’ shared experiences and then applied grounded theory to develop a set of conjectures derived inductively from participants’ responses. Using Spradley’s (1979) domain analysis to categorize common themes and patterns, the major domains of Weather Considerations and Expectations, Thoughts and Actions, and Postflight Experiences emerged. Major findings from the first domain revealed that as part of their preflight actions prior to departure, participants received a weather briefing, gave little consideration to overall weather conditions, neither expected nor anticipated IMC, and used a variety of communication resources to keep current with weather related issues. Major findings from the second domain revealed that participants recognized changes in the weather en route, used various communication resources to assess their current condition, reacted to IMC by trying to avoid and escape it, expressed feelings of trepidation about what they should do, were surprised over how the weather was not what they expected, and reverted to their training to get out of IMC. Major findings from the third domain revealed that participants’ postflight actions ranged from doing nothing to submitting a report to NASA’s ASRS, and that lessons learned included acquiring a heightened sense of situational awareness, a need to do a better job in alternative planning, and a greater appreciation for the weather. A comparison of these findings to past studies and theory are discussed, and implications and recommendations for practice and research are provided.