Ecological “surprises” are defined as unexpected findings about the natural environment. They are critically important in ecology because they are catalysts for questioning and reformulating views of the natural world, help shape assessments of the veracity of a priori predictions about ecological trends and phenomena, and underpin questioning of effectiveness of resource management. Despite the importance of ecological surprises, major gaps in understanding remain about how studies might be done differently or done better to improve the ability to identify them. We outline the kinds of ecological surprises that have arisen from long-term research programs that we lead in markedly different ecosystems around the world. Based on these case studies, we identify important lessons to guide both existing studies and new investigations to detect ecological surprises more readily, better anticipate unusual ecological phenomena, and take proactive steps to plan for and alleviate “undesirable” ecological surprises. Some of these lessons include: (i) maintain existing, and instigate new, long-term studies; (ii) conduct a range of kinds of parallel and concurrent research in a given target area; (iii) better use past literature and conceptual models of the target ecosystem in posing good questions and developing hypotheses and alternative hypotheses; and (iv) increase the capacity for ecological research to take advantage of opportunities arising from major natural disturbances. We argue that the increased anticipatory capability resulting from these lessons is critical given that ecological surprises may become more prevalent because of climate change and multiple and interacting environmental stressors.