Within burgeoning communities of the Global South, mountains of waste continue to pile skywards. In what is often known as ‘garbage cities’, waste management looms as a highly complex and intractable problem, with multiple dimensions that permeate the deepest fabric of society. Far removed from the more comprehensible challenges of the North, simplistic notions of the circular economy as a panacea are doomed to failure. In such highly informal and unstructured contexts, waste-pickers eke out an existence, supplemented by often futile attempts to introduce official policies, programs, and collection systems, accompanied by well-meaning NGOs and brave social entrepreneurs. As a result, waste may be accepted as an unchangeable way of life, impacting sanitation, health, well-being, and the ability of communities to escape the poverty trap. The paper highlights the necessity to fully understand and appreciate the complexities of such settings, where the many factors at play constitute a ‘wicked’ problem demanding holistic, system-wide approaches, with our ‘eyes wide open’ to the many pitfalls, barriers, and risks.