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Abstract Despite the ubiquity of eddies at the Mid‐Atlantic Bight shelf‐break front, direct observations of frontal eddies at the shelf‐break front are historically sparse and their biological impact is mostly unknown. This study combines high resolution physical and biological snapshots of two frontal eddies with an idealized 3‐D regional model to investigate eddy formation, kinematics, upwelling patterns, and biological impacts. During May 2019, two eddies were observed in situ at the shelf‐break front. Each eddy showed evidence of nutrient and chlorophyll enhancement despite rotating in opposite directions and having different physical characteristics. Our results suggest that cyclonic eddies form as shelf waters are advected offshore and slope waters are advected shoreward, forming two filaments that spiral inward until sufficient water is entrained. Rising isohalines and upwelled slope water dye tracer within the model suggest that upwelling coincided with eddy formation and persisted for the duration of the eddy. In contrast, anticyclonic eddies form within troughs of the meandering shelf‐break front, with amplified frontal meanders creating recirculating flow. Upwelling of subsurface shelf water occurs in the form of detached cold pool waters during the formation of the anticyclonic eddies. The stability properties of each eddy type were estimated via the Burger number and suggest different ratios of baroclinic versus barotropic contributions to frontal eddy formation. Our observations and model results indicate that both eddy types may persist for more than a month and upwelling in both eddy types may have significant impacts on biological productivity of the shelf break.