Resource fluxes at the stream-riparian interface are a vital contributor to both systems' energy budgets. The effect of distinct litter exposure patterns-direction of the riparia-stream movement and duration of exposure at each habitat-however, remains to be elucidated. In this field experiment, oak leaves in fine and coarse mesh bags were either exposed to a stream-to-riparia or riparia-to-stream movement sequence for distinct periods (2:6, 4:4, or 6:2 weeks). After 8 weeks, ash-free mass loss, microbial activity, and fungal biomass were compared in leaves undergoing inverse movement sequences (e.g., 2-week exposure to the riparian area at the beginning vs. end of the colonization period). Mass loss in coarse mesh bags was negatively affected when leaves were previously exposed to a short (2 weeks) terrestrial pre-conditioning period, despite higher microbial activity and fungal biomass, when compared to the inverse movement. This effect on mass loss was neutralized by longer terrestrial exposures that likely allowed for a more thorough conditioning of the leaves, through extended leaching and terrestrial microbial colonization. Our results suggest that terrestrial pre-conditioning periods of < 2 weeks lead to litter-quality legacy effects in tough leaves, to which aquatic communities respond through lower substrate degradation efficiency, hindering stream decomposition. Contrastingly, oak aquatic pre-conditioning, regardless of duration, provides riparian communities with a high-quality resource, promoting litter processing through grazing behavior. As climate-induced hydrological shifts may result in altered provision/quality of detritus subsidies at the stream-riparia interface, we suggest that assessments of decomposition dynamics should consider the entire litter conditioning history.