There is a prominent line of work in natural language semantics, rooted in the work of Hamblin, in which the meaning of a sentence is not taken to be a single proposition, but rather a set of propositions—a set of alternatives. This allows for a more fine-grained view on meaning, which has led to improved analyses of a wide range of linguistic phenomena. However, this approach also faces a number of problems. We focus here on two of these, in our view the most fundamental ones. The first has to do with how meanings are composed, i.e., with the type-theoretic operations of function application and abstraction; the second has to do with how meanings are compared, i.e., the notion of entailment. Our aim is to reconcile what we take to be the essence of Hamblin’s proposal with the more orthodox type-theoretic framework rooted in the work of Montague in such a way that both the explanatory utility of the former and the solid formal foundations of the latter are preserved. Our proposal builds on insights from recent work on inquisitive semantics, and it also contributes to the further development of this framework by specifying how the inquisitive meaning of a sentence may be built up compositionally.