The present paper analyzes and compares the use of clefted wh-interrogatives in spoken Madrid Spanish, Puerto Rican Spanish and Brazilian Portuguese. In a first step, a typology of the discourse functions of clefted wh-interrogatives is established. This typology is partially governed by the strength of the presupposition of the proposition of the wh-interrogative. The results suggest the existence of two distinct constructionalization processes 1 March 2021. First, in the Spanish dialects, clefted wh-interrogatives with copula deletion are specialized in the expression of interactional challenges. Second, both Puerto Rican Spanish and Brazilian Portuguese evidence a change in the use of information-seeking clefted wh-interrogatives towards contexts in which the proposition of the interrogative is not activated. Consequently, in these dialects clefted wh-interrogatives can be used to establish questions not related to the current Question Under Discussion. However, this semantic change can be characterized as a constructionalization process only in Brazilian Portuguese.