A recent experiment [Appl. Phys. Lett. 83, 213 (2003)] indicated that filaments created in femtosecond high-power pulses propagating in air are surprisingly robust when interacting with microscopic water droplets. We present numerical modeling of the dynamics of the filament-droplet interaction. Our simulation results provide further insight into the interplay between the filament's core and the wide transverse pedestal of the pulse. It is shown that the robustness of the filament comes from the transverse low-intensity pedestal that controls the formation of the central hot spot. Implications for penetration of wide, high-power beams through obscurants are discussed.