Rhetorical questions (RhQs) are a complex phenomenon at the interface of pragmatics, prosody and syntax, which requires reasoning on intentions and goals, and which involves a mismatch between literal and intended meaning. In Italian, RhQs can be marked by optional particles and verbal morphology. We investigated when children aged 6-9 acquire the relevant patterns of optional modification and exploit them in the appropriate pragmatic context. In an elicited production study with 84 monolingual and 88 Italian–German bilingual children, we found that development in monolinguals was determined by age with a progression between 6 and 9 years, while bilingual development was influenced by proficiency in the heritage language and dominance more generally. These results are in line with Tsimpli's (2014) proposal that “very-late-acquired phenomena”, especially interface domains, depend on their timing in acquisition. Unlike for other pragmatic phenomena, such as irony and conversational competence, there was no evidence for a bilingual advantage.