Perpetually planning the Guayuriba River basin for nearly two decades has allowed mining companies to continue extracting gravel, amidst uncertain flooding dynamics; oil companies to continue discharging production waters, despite uncertain water quality; and palm oil plantations to continue large-scale irrigation, notwithstanding uncertainties in water use and availability. Drawing on ethnographic fieldwork and semi-structured interviews in the Guayuriba River basin of the Eastern Foothills of Colombia, we discuss the temporality of planning, the rituals of expertise and public participation, and the accrual of uncertainties related to flooding, water quality, and water use and availability. Uncertainties have been perpetuated, accumulated, obscured, and met with a lack of will throughout the continual revision and adjustment of the river-basin planning document. While peoples and natures are made to wait, perpetual planning has in fact led to a tacit authorization of increased resource extraction despite concerns of environmental degradation. By embracing uncertainty as an inherent aspect of the system, we can envision a planning process that would prioritize local knowledge and experiential insights over detached expertise, reshaping the dynamics of knowledge dissemination in the region and mitigating the potential for corrupt practices, allowing our engagement with uncertainty to evolve as we interact with the world.