Islands are bounded systems, often plagued with several sustainability challenges of limited land and resource availability, as well as pressing waste management issues. Despite these known problems, research aiming to help develop proper e-waste management systems for small island nations is scarce. Focusing on five Caribbean island states, this study provides the first comprehensive view of e-waste generation trends in an island context and explores the factors driving those trends. The study estimates Electrical and Electronic Equipment (EEE) flows for the five island cases over a period of 60 years (1965–2025), including e-waste that these flows have and will generate. A dynamic material flow analysis (MFA) approach has been used to estimate these flows and stocks for 206 product types. The results show that the five Caribbean islands produced double the e-waste per capita per year, i.e., 13 kg/cap/year compared to global average of 6.1 kg/cap/year in 2016. The aggregated amount of e-waste generated per year on these five islands seems to significantly rise in future: from 27,500 tonnes in 2010 to an estimated amount of 59,000 tonnes in 2025. This considerable estimated e-waste generation rate, when not properly managed, is not only harmful for the local environment, but also translates into considerable health impacts and loss of valuable resources. From a sustainability perspective, small islands should consider moving away from a linear to a circular economy that will limit waste generation as well as reliance on the supply of virgin materials from outside.