Background: Air carriers, but not general aviation, have long employed in-flight data to identify risks/implement corrective measures for improved safety. Herein, using in-flight data, aircraft (in non-instrument-rated private pilots (PPLs) ownership) operations in two potentially hazardous environments (mountains, degraded visibility) were researched for safety practice deficiencies. Four questions were posed, the first two related to mountainous terrain operations: were aircraft (a) flown with hazardous ridge-level winds, (b) within gliding distance of level terrain? Regarding degraded visibility, did aviators (c) depart with low cloud ceilings (≤3,000 ft.), (d) fly at night away from urban lighting? Methods: The study cohort comprised: (a) single engine aircraft in sole PPL proprietorship (b) registered in Automatic Dependent Surveillance-Broadcast (ADS-B-Out) equipage-required locations prone to low cloud ceilings in three mountainous states. ADS-B-Out data for cross-country flights (>200 nm) were collected. Results: 250 flights (50 airplanes) were tracked (spring/summer 2021). For aircraft transiting areas subject to mountain winds influences, 65% completed one/multiple flights with potentially hazardous ridge-level winds. Two thirds of airplanes traversing mountainous topography would have, for at least one flight, been unable to glide to level terrain with a powerplant failure. Encouragingly, flight departures for 82% of the aircraft were with >3,000 ft. cloud ceilings. Likewise, flights for >86% of the study cohort were undertaken during daylight. Employing a risk scale, operations for 68% of the study cohort did not exceed low-risk (i.e., ≤1 unsafe practice) and high-risk flight(s) (three concurrent unsafe practices) were rare (4% of airplanes). In log-linear analysis, no interactions were evident between the four unsafe practices (p = 0.602). Discussion: Hazardous winds and inadequate engine failure planning were identified as safety deficiencies for general aviation mountain operations. Practical Application: This study advocates for the expanded use of ADS-B-Out in-flight data to inform safety deficiencies/implement corrective measures toward improving general aviation safety.