Highly experienced pilots, including airline first officers and captainsm, bring valuable skills to general aviation, but also a unique set of risk factors when transitioning into high-performance, complex, and turbocharged aircraft. This session explores the pro pilot trap, where habits developed in highly structured, crew-based, turbine environments can degrade safety in single-pilot GA operations. Drawing on real-world instructional experience with airline and charter crewmembers rejoining the GA ranks, this presentation identifies key vulnerabilities, including automation dependency, checklist discipline mismatches, degraded stick-and-rudder skills, and overconfidence in aircraft capability, particularly in turbocharged operations where performance can mask weather and energy management risks. Attendees will learn how these risks develop and manifest across all phases of flight, from preflight planning through postflight debrief, and how to address them through targeted instruction. Emphasis is placed on scenario-based training, rebuilding single-pilot resource management (SRM), refining decision-making, and teaching effective engine and weather management strategies. This session provides practical tools CFIs can immediately apply to improve safety, efficiency, and proficiency when working with experienced pilots transitioning back into GA. NAFI Session type: Forum — Skyfarer is not affiliated with the Experimental Aircraft Association (EAA) or EAA AirVenture Oshkosh. This session is listed for informational purposes from the official AirVenture 2026 schedule. Times and locations can change during the event — verify on the official session page: https://events.rdmobile.com/Sessions/Details/3580980