A paradox at the heart of language acquisition research is that, to achieve adult-like competence, children must acquire the ability to generalize verbs into non-attested structures, while avoiding utterances that are deemed ungrammatical by native speakers. For example, children must learn that, to denote the reversal of an action, un- can be added to many verbs, but not all (e.g., roll/unroll; close/*unclose). This study compared theoretical accounts of how this is done. Children aged 5–6 (N = 18), 9–10 (N = 18), and adults (N = 18) rated the acceptability of un- prefixed forms of 48 verbs (and, as a control, bare forms). Across verbs, a negative correlation was observed between the acceptability of ungrammatical un- prefixed forms (e.g., *unclose) and the frequency of (a) the bare form and (b) alternative forms (e.g., open), supporting the entrenchment and pre-emption hypotheses, respectively. Independent ratings of the extent to which verbs instantiate the semantic properties characteristic of a hypothesized semantic cryptotype for un- prefixation were a significant positive predictor of acceptability, for all age groups. The relative importance of each factor differed for attested and unattested un- forms and also varied with age. The findings are interpreted in the context of a new hybrid account designed to incorporate the three factors of entrenchment, pre-emption, and verb semantics.