This paper provides the first comprehensive evidence that the return extrapolation behavior of investors leads to biases in the expectations of volatility. Lower past returns are associated with higher expectations of volatility when using the physical, risk-neutral, and survey measures to estimate volatility expectations. Consistent with the return extrapolation framework, recent past returns have a larger impact than distant past returns on volatility expectations. Biases in volatility expectations are (i) distinct from extrapolating past realized volatility, (ii) asymmetrically induced by recent past negative returns, and (iii) lead investors to pay more to insure against the perceived higher expected volatility.