Counterpossibles are counterfactuals with necessarily false antecedents. The problem of counterpossibles is easiest to state within the "nearest possible world" framework for counterfactuals: on this approach, a counterfactual is true (roughly) when the consequent is true in the "nearest" possible world where the antecedent is true. Since counterpossibles have necessarily false antecedents, there is no possible world where the antecedent is true. On the approach favored by Lewis, Stalnaker, Williamson, and others, counterpossibles are all trivially true. I introduce several arguments against the trivial approach. First, it is counter-intuitive to think that all counterpossibles are true. Second, if all counterpossibles were true, then we could not make sense of their use in logical, philosophical, or mathematical arguments. Making sense of the role of sentences like these requires that they not have vacuous truth conditions. The account of counterpossibles I ultimately favor is an extension of the "nearest possible world" semantics discussed above. The Lewis/Stalnaker account is supplemented with the addition of impossible worlds, and the nearness metric is extended to range over these impossible worlds as well as possible worlds. Thus, a counterfactual is true when its consequent is true in the nearest world where the antecedent is true; if the counterfactual's antecedent is impossible, then the nearest world in question will be an impossible world. Once the framework of impossible worlds and similarity is in place, we can put it to use in the analysis of other philosophical phenomena. I examine one proposal that makes use of a theory of counterpossibles to develop an analysis of the notion of metaphysical dependence.