We discuss oceanic drift as relevant to applications in operational oceanography using examples from recent field experiments to highlight some of the challenges in modeling drift trajectories. Short-term predictions are important in time-critical operations, for example, for oil spill mitigation; hence, it is important that the transient response of the upper ocean to atmospheric forcing is modeled correctly. We emphasize the impact of surface waves and discuss the coupling between waves and mean flow in some detail. Because many objects of interest (e.g., person in water, oil spills) are in the wave zone, a better understanding of the details of the dynamics at the air-sea interface is needed. A clear separation of the forcing on such objects due to wind, waves, and ocean currents is needed in drift models, both to reduce dependence on empirical formulae and to make better use of drift data collected in field experiments.