This paper readdresses one of the most conspicuous syntactic traits of varieties of Caribbean Spanish that has been on the research agenda ever since almost a hundred years ago: the preverbal occurrence of subjects in interrogatives with a fronted simple non-subject argumental wh-expression. In an attempt to shed more light on the still highly controversial issues of the frequency of whSV order and the kind(s) of preverbal subject, the present paper initially gathers claims regarding these issues as well as examples from the literature and then presents the corresponding results from a refined large-scale quantitative analysis of natural speech from colloquial Dominican Spanish, hereby filling a long-standing lacuna. Furthermore, the paper discusses previous approaches and shows that none of these are free from problems. Drawing on relevant aspects of earlier approaches and building on insights into the morpho-syntactic status of subject pronouns as well as word order in medieval French, the paper eventually argues that whSV order in Dominican, and by extension, in other varieties of Caribbean Spanish, follows from ongoing morpho-syntactic changes that possibly result in the resetting of the null subject parameter: the development of a paradigm of weak subject pronouns, the concomitant establishment of a dedicated subject position, SpecTP, and the overall strong tendency towards SV order.