Flood management and adaptation are important elements in sustaining farming production in the Vietnamese Mekong Delta (VMD). While over the past decades hydraulic development introduced by the central government has substantially benefited the rural economy, it has simultaneously caused multiple barriers to rural adaptation. We investigate the relational practices (i.e., learning interactions) taking place within and across the flood management and adaptation boundaries from the perspective of social learning. We explore whether and how adaptive knowledge (i.e., experimental and experiential knowledge) derived from farmers’ everyday adaptation practices contributes to local flood management and adaptation policies in the selected areas. We collected data through nine focus groups with farmers and thirty-three interviews with government officials, environmental scientists, and farmers. Qualitative analysis suggests that such processes are largely shaped by the institutional context where the boundary is embedded. This study found that while the highly bureaucratic operation of flood management creates constraints for feedback, the more informal arrangements set in place at the local level provide flexible platforms conducive to open communication, collaborative learning, and exchange of knowledge among the different actors. This study highlights the pivotal role of shadow systems that provide space for establishing and maintaining informal interactions and relationships between social actors (e.g., interactions between farmers and extension officials) in stimulating and influencing, from the bottom-up, the emergence of adaptive knowledge about flood management and adaptation in a local context.