A migrating bird's response to wind can impact its timing, energy expenditure, and path taken. The extent to which nocturnal migrants select departure nights based on wind (wind selectivity) and compensate for wind drift remains unclear. In this paper, we determine the effect of wind selectivity and partial drift compensation on the probability of successfully arriving at a destination area and on overall migration speed. To do so, we developed an individual-based model (IBM) to simulate full drift and partial compensation migration of juvenile Willow Warblers (Phylloscopus trochilus) along the southwesterly (SW) European migration corridor to the Iberian coast. Various degrees of wind selectivity were tested according to how large a drift angle and transport cost (mechanical energy per unit distance) individuals were willing to tolerate on departure after dusk. In order to assess model results, we used radar measurements of nocturnal migration to estimate the wind selectivity and proportional drift among passerines flying in SW directions. Migration speeds in the IBM were highest for partial compensation populations tolerating at least 25% extra transport cost compared to windless conditions, which allowed more frequent departure opportunities. Drift tolerance affected migration speeds only weakly, whereas arrival probabilities were highest with drift tolerances below 20°. The radar measurements were indicative of low drift tolerance, 25% extra transport cost tolerance and partial compensation. We conclude that along migration corridors with generally nonsupportive winds, juvenile passerines should not strictly select supportive winds but partially compensate for drift to increase their chances for timely and accurate arrival.