Human security outcomes of cannabis decriminalisation are important for small island developing states. This study uses a convergent parallel mixed-methods research design and comparative case analysis of Jamaica and St. Vincent and the Grenadines to develop a results matrix to evaluate the human security outcomes of cannabis decriminalisation. The findings indicate that St. Vincent and the Grenadines' context-sensitive approach has been more effective in providing livelihood opportunities for traditional farmers. In comparison, Jamaica's reform, using a people-centred approach and supported by a revised four-point plan, has struggled to integrate traditional farmers into its regulatory framework. Both states demonstrated sensitivity to cannabis use through social justice via expungement legislation, and health security through medical access. However, challenges remain in measuring the impact on health security in St. Vincent and the Grenadines. Biennial surveys capturing key variables can address this deficit by identifying policy gaps and guiding adaptive approaches. The study contributes to the discourse on drug reform and evaluation methodology as the development of a results matrix can assess human well-being and establish benchmarks for evaluating state progress in enhancing human security. The findings offer insights for policymakers, stakeholders, and evaluators to establish a secure cannabis industry aligned with human security principles.