© 2020 by the authors. The very diverse character of General Aviation (GA) within Australia poses challenges for its effective management of risk and safety in the sector. Improvements for human performance and perceptions of safety within the maintenance environment are among the areas which regulators have targeted for continuous improvement. This paper provides a timely empirical exploration of maintenance engineer perspectives around: (1) Changes in the role of the regulator/regulation that have impacted the sector and diminished safe operations; and (2) specific practical and operational challenges that the GA industry must deal with to sustain safe operations going forward. A thematic analysis of transcribed qualitative data revealed five key themes and identified a number of key issues from sector changes including a decline in training and education, drift in working practices, and wider power-distance gap. Issues with auditing and bureaucratization, negative safety climate, and underlying values and philosophies were also found. Practical and operational challenges going forward included an array of concerns associated with safety, the mismatch between GA and commercial aviation, workforce development and the financial burden in the sector. The results draw attention to the interconnectedness between various components of the GA system, and carry timely implications for regulation in the GA sector. Future research directions are discussed.