Objectives: Type 2 diabetes (T2D) has been increasingly associated with a heightened risk of various gastrointestinal (GI) cancers. This narrative review aims to synthesise current evidence on the link between newly diagnosed T2D and GI malignancies, and to propose a clinical framework for risk-adapted cancer vigilance. Methods: We conducted a narrative review of the literature focusing on the association between T2D and GI cancers, including colorectal, pancreatic, liver, gastric, and biliary malignancies. We examined shared risk factors, underlying biological mechanisms, and emerging insights into pathophysiology. Results: Epidemiological and mechanistic studies suggest that chronic hyperglycaemia, hyperinsulinemia, insulin resistance, inflammation, and gut microbiota alterations contribute to cancer development in patients with T2D. Despite these findings, current screening guidelines do not provide T2D-specific recommendations for GI cancer surveillance. Conclusions: T2D is an emerging risk factor for several GI malignancies. Clinicians should be aware of this association and consider individualised assessment in newly diagnosed patients. The proposed algorithm is intended to stimulate further discussion and guide future research. Prospective studies are needed to evaluate the effectiveness and feasibility of targeted screening strategies in this high-risk population.