AbstractI offer a novel solution to the problem of counterfactual skepticism: the worry that all contingent counterfactuals without explicit probabilities in the consequent are false. I argue that a specific kind of contextualist semantics and pragmatics for would‐ and might‐counterfactuals can block both central routes to counterfactual skepticism. One, it can explain the clash between would‐ and might‐counterfactuals as in: (1) If you had dropped that vase, it would have broken. and (2) If you had dropped that vase, it might have safely quantum tunneled to China. Two, it can explain why counterfactuals like (1) can be true despite the fact that quantum tunneling worlds are among the most similar worlds. I further argue that this brand of contextualism accounts for the data better than other existing solutions to the problem.