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This study examined the effect of video weather training products on general aviation (GA) pilot flight behavior. Fifty pilots participated. Training products were two popular GA weather training videos, plus a non-weather video as control. Pilots watched one video. Then, in the CAMI flight simulator, they flew a challenging 1.5-h visual flight rules (VFR) mission. Along the route, terrain rose slowly, with cloud bases squeezing pilots between ground and clouds. The control group penetrated significantly farther into the deteriorating weather. Otherwise, no significant safety differences were observed for time spent in instrument meteorological conditions (IMC), time scud running, or time below 500’ ground clearance. Neither instrument rating nor locality of pilot residence appeared to affect these safety variables. Flight behavior—complete penetration of the weather versus diverting—could be predicted for 80% of pilots, using a model with training product + initial takeoff hesitation + pilot age.