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Educational disparities within the Dominican Republic (DR) have long-standing origins rooted in economic, political, and social inequity. Addressing these challenges has necessarily called for capacity building with respect to educational materials, high-quality instruction, and structural resourcing. Generative AI tools like ChatGPT have begun to pique the interest of Dominican educators due to their perceived potential to bridge these educational gaps. However, a substantial body of AI fairness literature has documented ways AI disproportionately reinforces power dynamics reflective of jurisdictions driving AI development and deployment policies, collectively termed the AI Global North. As such, indiscriminate adoption of this technology for DR education, even in part, risks perpetuating forms of digital coloniality. Therefore, this paper centers embracing AI-facilitated educational reform by critically examining how AI-driven tools like ChatGPT in DR education may replicate facets of digital colonialism. We provide a concise overview of 20th-century Dominican education reforms following the 1916 US occupation. Then, we employ identified neocolonial aspects historically shaping Dominican education to interrogate the perceived advantages of ChatGPT for contemporary Dominican education, as outlined by a Dominican scholar. This work invites AI Global North & South developers, stakeholders, and Dominican leaders alike to exercise a relational contextualization of data-centric epistemologies like ChatGPT to reap its transformative benefits while remaining vigilant of safeguarding Dominican digital sovereignty.