This paper presents an experimental and analytical investigation into the dominant noise generation mechanisms of unmanned Fixed-wing Vertical Take-Off and Landing (VTOL) propeller–wing configurations during takeoff. This paper reports the velocity measurements made in the close vicinity of a scale-model propeller adjacent to a flat plate or wing, aimed at understanding and characterising its dominant noise generation mechanisms. This paper identifies two main interaction mechanisms. The first is a purely acoustical phenomenon whereby the wing acts as an image source causing strong interference between the direct and image noise sources due to the propeller. The second is a significant noise increase resulting from the unsteady blade loading that occurs when the blade passes over the wing at lower vertical separation distances. Other, more minor noise sources from the propeller and the wing are also discussed in this paper.