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Hurricane Lili (28 Sept) formed in the northwest Caribbean Sea and followed Isidore's track. Due to deep, warm layers in this oceanic regime, no significant SST cooling (< 0.5oC) was observed from the ocean profilers. Lili moved over the western tip of Cuba across the Loop Current and directly over the Isidore ocean grids. In the Loop Current, OHC loss was less than 7 KJ cm-2 with a decrease in SST of 1oC. On 2 Oct, Lili rapidly intensified to a Category 4 storm across a strong OHC gradient where surface wind speeds exceeded 50 m s-1. In the Loop Current regime, the oceanic response was considerably less than that observed to northwest of the Loop Current due to the horizontal advection of deep warm layers by currents of 1.5 m s-1. In situ and satellite-derived fields indicated an additional OHC loss of >30 KJ cm-2 north of the Loop Current where the upper ocean cooled by more than 2oC due to strong vertical current shears across the base of the oceanic mixed layer. Subsequently, Lili decreased to a cat-1 storm upon encountering the cooler wake of Isidore in the northern Gulf of Mexico, increased wind shear, and drier air prior to landfall on 3 Oct. Measurements acquired from these research flights are providing insights into the role of the three-dimensional atmospheric structures encountering a warm and sustained heat source such as the Loop Current and warm subtropical water emanating from the northwest Caribbean Sea.