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A total of 46 contextual factors were identified and examined from the reviewed research literature. The study examined and determined the presence of the 46 contextual factors, frequencies, and manifestations in the GA VFR-into-IMC Aviation Accident Reports (AARs) archived in the National Transportation Safety Board (NTSB) online safety database. Significant relationships were identified among the contextual factors and pilot age, flight experience, weather, flight conditions, time of day, and certification level using point biserial and phi correlations. Contextual factor significant effects on the crash distance from departure and crash distance from the planned destination were revealed using multiple regression. A qualitative methodology was used on secondary data. Three subject matter experts (SMEs) for the main study analyzed a sample of 85 accidents for the presence of the 46 contextual factors. Raters then reported the presence of the contextual factors and provided opinions on how the contextual factors were manifested. Qualitative analysis revealed the presence of 37 out of 46 contextual factors. Highest frequency factors included number of passengers on board (CF29), accident time of day (CF1), crash distance from the planned destination (CF15), not filing of a flight plan (CF21), and underestimating risk (CF43). Raters described numerous manifestations of the contextual factors including 62% of the accident flights had passengers on board the aircraft (CF29). Quantitative analysis discovered several significantly weak to moderate relationships among pilot age, flight experience, weather, flight conditions, time of day, certification level, and the contextual factors. Several contextual factors had significant effects on the crash distance from departure and crash distance from the planned destination. Findings indicated the contextual factors were extensive in GA accidents. Additional research should focus on all flight domains, including further study of GA Part 91 VFR-into-IMC accidents. It is recommended the GA Part 91 pilot community be trained on the contextual factors assessed.