This podcast explores the concept of maintenance moonlighting, where certified aviation technicians provide their skills to multiple employers to address industry personnel shortages. While this flexibility offers financial and professional benefits, it necessitates strict adherence to federal safety regulations, specifically regarding drug and alcohol testing programmes. Technicians and contractors must ensure they are covered by an approved testing scheme whenever they perform safety-sensitive functions for air carriers or sightseeing operators. The podcast highlights that even minor maintenance tasks require documented compliance with 14 CFR part 120 to avoid severe legal repercussions. Ultimately, the authors stress that professional versatility in aerospace must be balanced with meticulous regulatory oversight and contract management. This ensures that independent work does not compromise aviation safety standards or the technician’s professional certification.