Approximately two thirds of migratory songbirds in eastern North America negotiate the Gulf of Mexico (GOM), where inclement weather coupled with no refueling or resting opportunities can be lethal. However, decisions made when navigating such features and their consequences remain largely unknown due to technological limitations of tracking small animals over large areas. We used automated radio telemetry to track three songbird species (Red-eyed Vireo, Swainson's Thrush, Wood Thrush) from coastal Alabama to the northern Yucatan Peninsula (YP) during fall migration. Detecting songbirds after crossing ∼1,000 km of open water allowed us to examine intrinsic (age, wing length, fat) and extrinsic (weather, date) variables shaping departure decisions, arrival at the YP, and crossing times. Large fat reserves and low humidity, indicative of beneficial synoptic weather patterns, favored southward departure across the Gulf. Individuals detected in the YP departed with large fat reserves and later in the fall with profitable winds, and flight durations (mean = 22.4 h) were positively related to wind profit. Age was not related to departure behavior, arrival, or travel time. However, vireos negotiated the GOM differently than thrushes, including different departure decisions, lower probability of detection in the YP, and longer crossing times. Defense of winter territories by thrushes but not vireos and species-specific foraging habits may explain the divergent migratory behaviors. Fat reserves appear extremely important to departure decisions and arrival in the YP. As habitat along the GOM is degraded, birds may be limited in their ability to acquire fat to cross the Gulf. migration | ecological barrier | Gulf of Mexico | songbirds | weather D uring migration, animals encounter ecological barriers, inhospitable environmental features that prevent or impede movement due to increased risk of mortality from starvation, predation, collision, and severe environmental conditions (e.g., weather for aerial migrants, aquatic temperature or chemical gradients for aquatic migrants) (1-5). Because barriers can have important consequences on survival and future reproductive success (6), animals have evolved behavioral, morphological, and/or physiological means to safely negotiate them (7-9). Barriers can include large geographic features (e.g., large water bodies, deserts, mountains), inhospitable land cover types (e.g., agricultural "deserts"), anthropogenic structures (e.g., tall buildings, towers, dams, weirs), and unfavorable weather and aquatic conditions (e.g., droughts, storms, strong temperature gradients), although the extent to which any of these functions as a barrier to migration varies (4,5,(10)(11)(12).Approximately two thirds of all songbird species and millions of individuals breeding in eastern Canada and the United States encounter the Gulf of Mexico (GOM) while migrating to tropical or subtropical wintering grounds in the Caribbean, Mexico, and Central and South America (13). Unfavorable weather conditions combine...