Stream and river ecosystems provide subsidies of emergent adult aquatic insects and other resources to terrestrial food webs, and this lotic–land subsidy has garnered much attention in recent research. Here, we critically examine a list of biotic and abiotic variables—including productivity, dominant taxa, geomorphology, and weather—that should be important in affecting the nature of these subsidy dynamics between lotic and terrestrial ecosystems, especially the pathway from emergent aquatic insects to terrestrial predators. We also explore how interactions between these variables can lead to otherwise unexpected patterns in the importance of aquatic subsidies to terrestrial food webs. Utilizing a match-mismatch framework developed previously, we identify how these variables and interactions may be affected by a broad suite of stressors in addition to contaminants: climate change, land-use conversion, damming and water abstraction, and species invasions and extinctions. These stressors may all act to modify and potentially exacerbate the effects of contaminants on subsidies. The available literature on many variables is sparse, despite strong theoretical underpinnings supporting their importance for lotic–land subsidies. Notably, these understudied variables include those related to physical geomorphology and the structure of the stream/river and floodplain/riparian zone as well as species-specific interactions between aquatic and terrestrial organisms. We suggest that more explicit characterization of these variables and more research directly linking broad-scale stressors to subsidy resource–consumer interactions can help provide a more mechanistic understanding to lotic–land subsidy dynamics within a changing environment.