To varying degrees, Caribbean countries are grappling with the issue of privacy and data protection. Countries that have more recent frameworks have been struggling to fully operationalise all of the provisions, whilst there are others that have not adopted current best practice in the space. With information privacy specialists, Allison James of Barbados, and Rishi Maharaj of Trinidad and Tobago, we explore privacy and data protection trends and developments across the Caribbean region. During our conversation, we discuss: how privacy and data protection have evolved over the past few years; the current status of regulatory enforcement; areas of divergence or contradiction that multinational companies operating across the Caribbean must navigate; and trends or emerging developments that the Caribbean region may need to consider.