Urban environments impose novel selection pressures with varying impacts across species and life history stages. The post‐fledging stage for migratory passerines, defined as the period of time from when hatch‐year birds fledge until their first migration, is a poorly understood component of annual productivity that potentially limits population growth. We studied two migratory passerines with positive and negative population responses to urbanization, respectively: Gray Catbird (Dumetella carolinensis) and Wood Thrush (Hylocichla mustelina). Our goals were to estimate post‐fledging survival rates for urban bird populations and determine which features of the urban landscape impact mortality risk during the post‐fledging stage. From 2012–2014, we tracked 127 fledglings (60 Gray Catbirds and 67 Wood Thrushes). Over 55 days after fledging, cumulative survival of Gray Catbirds (0.32 [95% CI: 0.22–0.47]) was approximately half that of Wood Thrushes (0.63 [95% CI: 0.52–0.75]). Thus, survival rates during the post‐fledging stage, taken in isolation, do not explain differential trajectories of Gray Catbird and Wood Thrush populations in urban environments. Most mortality (86%) for both species was due to predation. However, after reaching independence from parental care, 6 birds (9.4% of mortalities) died of anthropogenic causes (e.g. building, car strikes). Crossing roads significantly increased mortality risk, but increasing daily movement distance decreased mortality risk. Our results raise the question of whether anthropogenic sources of mortality are compensatory or additive to natural mortality; we emphasize the need to monitor fledgling survival beyond the parental‐dependence stage in order to fully understand the impacts of anthropogenic hazards on juvenile birds.