A mechanism for the cross-frontal entrainment of plankton by a buoyant plume influenced by wind stress is described and tested using an idealized numerical model. Under the right circumstances, plankton may enter a buoyant plume during an upwelling wind stress, then be transported shoreward during a subsequent downwelling wind stress. In order for the plankton to enter the plume, they must swim upward at a velocity (wp) bounded by Hplume/T < wp < κ/ Hmix where Hplume is the thickness of the buoyant plume, Hmix is the thickness of the upper oceanic mixed layer (Hmix > Hplume), κ is the magnitude of vertical mixing within the mixed layer, and T is the time between upwelling and downwelling events. In words, this equation states that the plankton must swim slow enough so that they are evenly distributed through the mixed layer, so that the buoyant plume may override the plankton patch during upwelling. Once the plume has overridden the patch, in order to enter the plume, the plankton must swim fast enough to be able to enter the plume in the time while it is over them. These two bounds on the swimming rate suggest that, given various physical parameters, there may be a range of swimming speed that will maximize entrainment into a plume. Numerical experiments corroborate the feasibility of the proposed mechanisms and associated scaling.