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The risk of an accident during general aviation (GA) flight increases when pilots are required to make unexpected diversions. Specifically, a diversion may result in loss of situation awareness (SA). Loss of SA is associated with controlled flight into terrain,incorrect trajectory for orbiting or landing, or becoming lost en route. In the present study, 44 GA pilots (aged 41 to 74 years) flew a cross-country route in a Cessna 172 simulator and encountered an unexpected diversion to an alternate aerodrome. The outcome measure consisted of a diversion management score. Significant predictors of diversion management were pilot age and license, a measure of prospective memory in the cockpit, and response times from an executive cognitive function subtest of the CogScreen-AE. A model of performance derived from a “best subsets” linear modeling algorithm included pilot license, prospective memory, and executive function. Importantly, less skill in managing the diversion also predicted a greater likelihood of critical incidents during the cross-country flight. Understanding the role of pilot factors in identifying those most at risk when flying an unexpected diversion can better prepare pilots for these rare events, and inform customized learning opportunities during check rides and flight instruction.