Cities in Asia are full of unexpected discoveries—metropolitan surprises. What might scholars learn by taking these surprises seriously? Panelists will discuss analytic discoveries that have emerged from a series of generative surprises encountered during their research in cities across Asia: a camel in a Gurgaon parking lot, and baroque McMansions in urban villages (Dharia); displaced farmers leading tours to showcase the suffering of life on the margins of Yangon (Wittekind); government officials and anti-establishment activists emphasizing “fun” in Singapore and junta-ruled Bangkok (Elinoff); the sudden appearance and mysterious disappearance of subversive graffiti designed to look like state slogans in Chongqing (Smith); and zany proposals proffered by Indonesian city officials to fight COVID using herbs and tonics while kampung residents themselves insist on local lockdowns and social distancing (Padawangi). What theoretical or analytic revelations might emerge by taking such surprises seriously? Focusing on urban surprises steers us away from hackneyed categories like “traditional” or “modern,” avoids loaded questions about authenticity, and pushes the boundaries regarding what counts as heritage. Surprises are central to what makes cities unique, but are almost always overlooked by planners, for whom they may represent unwanted disruption and disorder. Unexpected surprises in cities across Asia have a vital social role. They often suture the loose seams where planning fails; they fill in the gaps where straight lines run into rough edges. Attending to surprise avoids the pitfalls of nostalgia, for urban surprises are always renewing and regenerating the city. But in a world where cities everywhere are being subordinated to data-driven planning, and where various subversions of the established order may be incubating, the role of surprise deserves attention. Things surprising to scholars may not be so to locals. Panelists will thus reflect on how and why surprise redirected their understanding of urban life, and what it means for studying aesthetic or political agendas, insurgent or unconventional modes of citizenship, new political formations, religious change, social solidarity movements, or ways of occupying space. The panel form models the content of discussion: we seek to surprise each other with new and unplanned ways of thinking about cities.