Reverse pedal operational property in front crosswind flight condition is a potential hazard for accidents involving loss of tail rotor effectiveness (LTE), which is closely related to the main rotor (MR) wake interference on the tail rotor (TR). As understanding of this interaction is vital for the early warning strategy development, the MR wake influence effect on TR thrust and the effect of helicopter yaw stability are examined in this study. For this purpose, the comparison of TR thrust and flow field with wind azimuth and speed in front crosswind environment was performed by experiment and CFD simulation, respectively. Test campaign was performed at a 5.5   m × 4   m wind tunnel in the China Aerodynamics Research and Development Center using a high-position bottom-blade forward-rotating TR and a counterclockwise rotating MR to address the TR thrust under wind speeds of 8–22 m/s with 50°, 60°, and 70° wind azimuths. The influence of MR disc loading was also contrasted. CFD analysis was used to gain insight into the flow physics responsible for the interference effect. It was conducted with unsteady Reynolds-averaged Navier–Stokes simulations, where the MR using the actuator disk approach and the TR blade rotation was modeled via a sliding mesh method. Results indicated that the MR disc vortex has a remarkable interference effect on the TR aerodynamic performance characteristic and that the effect is sensitive to the wind speed, wind direction, and MR disc loading. The observed yaw instability is considered to be related to the lesser inflow introduced by the MR disc vortex due to the change in the relative position of the disc vortex filament and TR with the wind azimuth. The increase in TR thrust at moderate wind speeds is due to the increase in leading edge dynamic pressure caused by the opposite swirl direction of the disc vortex contrasted to the TR. The MR disc loading affects the TR thrust due to the change of disc vortex strength and position.