Little is known about presuppositional skills in pre-school years. Developmental research has mostly focused on children’s understanding of too and evidence is mixed: some studies show that the comprehension of too is not adult-like at least until school age, while more recent findings suggest that even pre-schoolers can interpret too-sentences in more age-appropriate tasks. Importantly, no study has tested directly, within the same experiment, pre-schoolers’ presupposition understanding in satisfaction versus accommodation, nor with respect to other trigger types. Yet, it is well known that adults’ processing of a presupposition is costlier when accommodation is required and that the type of trigger influences the processing demands. Therefore, both the trigger type and the contextual availability of a presupposition might influence young children’s comprehension. We tested this with a story completion task that assessed 3–5-year-olds’ comprehension of presuppositions activated by either regret or too in contexts that either satisfied the presupposition or required accommodation. Results reveal that pre-schoolers overall exhibit an understanding of presupposition. Crucially, this starkly improves between the age of 3 and 5 and the developmental trajectory depends on both context and trigger type: understanding the presupposition of regret seems easier than that of too for younger children, and less difficulties emerge when the context satisfies the presupposition. Thus, the development of presupposition comprehension in pre-schoolers depends both on the type of trigger and the contextual availability of the presupposition – satisfied versus requiring failure repair.