Some conjunctions simultaneously convey speakers' presuppositions about the validity of propositions uttered and assertions of particular interclausal relations. Because conveys belief, if + indicative, uncertainty and if + subjunctive, disbelief. While all three conjuctions assert positive entailment, unless, which like if + indicative presupposes uncertainty, asserts negative entailment or denial. The relationship between pragmatic knowledge and reasoning was explored by asking 12 males and 12 females at each of three ages (12, 15, adult) to solve written syllogisms containing the four conjunctions and evaluate single sentences for their pragmatic content. In the pragmatic task, belief was easier to detect than uncertainty or disbelief. Positive entailment was easier than negative entailment. Only entailment influenced syllogistic reasoning with unless harder than the positively entailed conjunctions. At each age linguistic comprehension of negative entailment was related to understanding valid implications in unless syllogisms. The relation between comprehension of pragmatic uncertainty and detection of uncertain conclusions in reasoning increased with age.