In this paper, we use antecedent-final conditionals to formulate two problems for parsing-based theories of presupposition projection and triviality of the kind given in Schlenker 2009. We show that, when it comes to antecedent-final conditionals, parsing-based theories predict filtering of presuppositions where there is in fact projection, and triviality judgments for sentences which are in fact felicitous. More concretely, these theories predict that presuppositions triggered in the antecedent of antecedent-final conditionals will be filtered (i.e. will not project) if the negation of the consequent entails the presupposition. But this is wrong: John isn’t in Paris, if he regrets being in Franceintuitively presupposes that John is in France, contrary to this prediction. Likewise, parsing-based approaches to triviality predict that material entailed by the negation of the consequent will be redundant in the antecedent of the conditional; but John isn’t in Paris, if he’s in France and Mary is with him is intuitively felicitous, contrary to these predictions. Importantly, given that the trigger appears in sentence-final position, both incremental (left-to-right) and symmetric versions of such theories make the same predictions. These data constitute a challenge to the idea that presupposition projection and triviality should be computed on the basis of parsing. This issue is important because it relates to the more general question as to whether presupposition and triviality calculation should be thought of as a pragmatic post-compositional phenomenon or as part of compositional semantics (as in the more traditional dynamic approaches). We discuss a solution which allows us to maintain the parsing-based pragmatic approach; it is based on an analysis of conditionals which incorporates a presupposition that their antecedent is compatible with the context, together with a modification to Schlenker’s (2009) algorithm for calculating local contexts so that it takes into account presupposed material. As we will discuss, this solution works within a framework broadly similar to that of Schlenker’s (2009), but it doesn’t extend in an obvious way to other parsing-based accounts (e.g. parsing-based trivalent approaches). We conclude that a parsing-based theory can be maintained, but only if we adopt a substantial change of perspective on the framework.