This experimental study focuses on the aerodynamic interaction between an over-the-wing (OTW) propeller and a wing boundary layer. An OTW propeller is positioned above the hinge line of a wing with a trailing-edge flap. Measurements are carried out with and without axial pressure gradients by deflecting the flap and by extending the flat upper surface of the wing in the streamwise direction, respectively. Surface-pressure taps, microphones, and particle image velocimetry are combined to quantify both the time-averaged and unsteady interaction effects. Results show that the propeller generates an adverse pressure gradient on the wing surface that scales linearly with thrust and decreases with increasing blade-tip clearance. The pressure gradient is partially caused by slipstream contraction, which decelerates the flow near the wall. Additionally, the surface-pressure fluctuations generated beneath the propeller blades and slipstream are stronger than the time-averaged pressure increase due to flow deceleration. Consequently, the propeller triggers flow separation over the hinge line when the flap is deflected. A parametric study of different propeller locations indicates that increasing the tip clearance is not an effective way to mitigate flow separation. However, displacing the propeller half a radius upstream of the hinge line creates a Coandă effect, which allows the flow to remain attached.