An autonomous underwater glider was deployed in March 2014 to sample the Gulf Stream and its adjacent shelf waters in the South Atlantic Bight, providing a new look at cross-shelf exchange associated with Gulf Stream dynamics. Observations collected over 4 weeks reveal significant cross-shelf exchange (up to 0.5 Sv) at the shoreward edge of the Gulf Stream, which was 2 orders of magnitude larger than estimates from long-term mean hydrographic conditions. Gulf Stream frontal eddies may have contributed to some of the largest fluxes of heat (0.5°C Sv) and salt (0.03 Sv g/kg) onto the shelf. We estimate that the largest upwelling event during the mission could have brought nitrate concentrations over 20 μM to within 125 m of the surface. This study demonstrates clear capabilities of autonomous underwater gliders for sampling in and near fast moving boundary currents to obtain unique and critical in situ observations effectively.