This chapter examines AI's role in Caribbean high school and college assessments, analyzing teacher and student perspectives. A quantitative study surveyed 160 students and 102 teachers via Google Forms in September 2023, investigating AI tool usage, its effects on grading and feedback, fairness, and ethical concerns. Key findings include students' prevalent use of Grammarly and ChatGPT and plagiarism software by teachers, with significant AI encounters at the high school level. Positive correlations emerged between teachers' views on AI's grading efficiency, optimism for its future, and students' appreciation for AI's timely feedback. Concerns about AI-induced discrimination showed no significant differences across countries or educational levels, highlighting ethics and transparency as crucial. The need for targeted AI integration training is emphasized, suggesting future research should address AI biases and explore new tools for enhancing Caribbean educational outcomes.