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Drops are retained or held on surfaces due to a retention force exerted on the drop by the surface. This retention force is a function of the surface tension of the liquid, drop geometry, and the contact angle between the drop and the surface. When external or body forces exceed the retention force, the drop begins to move. This work explores the conditions for which drop departure occurs on structured superhydrophobic surfaces in the presence of an applied shear flow. Drop departure is explored for five microstructured superhydrophobic surfaces, one nanostructured carbon nanotube surface and one smooth hydrophobic surface. Surface solid fractions range from 0.05 to 1.00, and measured static contact angles range from 121° to 161°. Droplet volumes of 5, 10, 20, 30, 40, and 50 μL are tested on each surface. For each experiment, increasing air velocity is applied to a droplet placed on a surface until the droplet departs. High-speed imaging is used to track droplet base length, height, cross-section area (as viewed from the side) and advancing/receding contact angles. Measurements of drop advancing and receding contact angles are reported at the point of departure, with increasing contact angle hysteresis observed prior to departure. Contact angle hysteresis is observed to be a good indicator of droplet mobility. Measurements of the average air velocity over the height of the droplet are determined at the point of departure for all conditions. The measured air velocity shows strong dependence on the surface solid fraction, and the required shear flow velocity decreases as the surface solid fraction decreases. This is most pronounced at very low solid fractions. A coefficient of drag for the departing drops in shear flow is calculated and is shown to decrease with increasing Reynolds number.