We derive an exact upper bound on the epidemic overshoot for the Kermack-McKendrick SIR model. This maximal overshoot value of 0.2984 · · · occurs at [Formula: see text]. In considering the utility of the notion of overshoot, a rudimentary analysis of data from the first wave of the COVID-19 pandemic in Manaus, Brazil highlights the public health hazard posed by overshoot for epidemics with near 2. Using the general analysis framework presented within, we then consider more complex SIR models that incorporate vaccination.