1.Matching the timing of life history transitions with ecosystem phenology is critical for the survival of many species, especially those undertaking long-distance migrations. As a result, whether and how migratory populations adjust timing of life history transitions in response to environmental variability are important questions in ecology and conservation. Yet the flexibility and drivers of life history transitions remain largely untested for migratory marine populations, which contend with the unique spatiotemporal dynamics and sensory conditions found in marine ecosystems. 2.Here, using an acoustic signature of blue whales’ regional population-level transition from foraging to breeding migration, we document significant interannual flexibility in the timing of this life history transition (spanning roughly four months) over a continuous six-year study period. 3.We further show that timing of this transition follows the oceanographic phenology of blue whales’ foraging habitat, with a later transition from foraging to breeding migration occurring in years with an earlier onset, later peak, and greater accumulation of biological productivity. 4.These results indicate that blue whales use flexible cues, likely including individual sensing of foraging conditions and long-distance vocal signals from conspecifics, to match timing of this population-level life history transition with interannual oceanographic variability in their vast and dynamic foraging habitat. The use of flexible cues in timing a major life history transition may be key to the persistence of this endangered population facing the pressures of rapid environmental change. 5.Further, these findings extend theoretical understanding of the flexibility and drivers of population-level migration beyond insights derived primarily from group-living and terrestrial migrants, illuminating the drivers and flexibility of a life history transition in a relatively solitary marine migrant.