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The transport of biodegradable dissolved organic carbon (bDOC) across land-water boundaries is central to supporting the ecological and biogeochemical functioning of freshwater ecosystems. Yet, we know little about how the generation and supply of terrestrial bDOC to streams and lakes is regulated by the physical, biological, and hydrological properties of the riparian interface. Here, we assessed how terrestrial, groundwater, and aquatic bDOC differ along flowpaths connecting riparian soils to a headwater boreal stream. We further tested how bDOC generation and supply differs among interfaces with distinct hydrogeomorphologies, as reflected by differences in soil properties, groundwater dynamics, and hydrological connectivity to the stream. We found that bDOC quantity declined sharply from terrestrial sources, to groundwater, to aquatic systems, and that these differences were associated with changes in the optical and chemical properties of the dissolved organic matter pool. However, bDOC generation and potential transport in groundwater varied across site types and reflected local differences in soil organic matter storage, depth to groundwater, and soil microbial community activity. Interface zones with organic-rich soils but weak hydrological connections had a large capacity to produce bDOC, but likely only laterally contributed organic resources during floods. By contrast, sites with stronger lateral hydrological connectivity served as persistent conduits for organic resources generated further upslope, even if the capacity to generate bDOC locally was weak. Overall, our results illustrate how hydrogeomorphic heterogeneity at the land-water interface can add spatial and temporal complexity to the generation and transfer of bDOC from soils to the inland water continuum.