The Kuroshio Extension System Study (KESS) provided 16 months of observations to quantify divergent eddy heat flux (DEHF) from a mesoscale-resolving array of current- and pressure-equipped inverted echo sounders. KESS observations captured a regime shift from a stable to unstable state. There is a distinct difference in the spatial structure of DEHFs between the two regimes. The stable regime had weak downgradient DEHFs. The unstable regime exhibited asymmetry along the mean path with strong downgradient DEHFs upstream of a mean trough at ~147°E. The spatial structure of DEHFs resulted from episodic mesoscale processes. The first 6 months were during the stable regime in which fluxes were associated with eastward-propagating 10-15-day upper meanders. After 6 months, the Kuroshio Extension underwent a regime shift from a stable to unstable state. This regime shift corresponded with a red shift in mesoscale phenomena with the prevalence of ~40-day deep externally generated eddies. DEHF amplitudes more than quadrupled during the unstable regime. Cold-core ring (CCR) formation, CCR–jet interaction, and coupling between ~40-day deep eddies were responsible for asymmetry in downgradient fluxes in the mean maps not observed during the stable regime. The Kuroshio Extension has prominent deep energy associated with externally generated eddies that interact with the jet to drive some of the biggest DEHF events. These eddies play an important role in the variability of the jet through eddy–mean flow interactions. The DEHFs that result from vertical coupling act in accordance with baroclinic instability. The interaction is not growth from an infinitesimal perturbation, but from the start is a finite-amplitude interaction.