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Fit-for-purpose mechanisms for developing land administration systems have been posited to be especially effective in resource strapped economies since these mechanisms quickly create the settings for economic as well as social and environmental development. Competition for depleted resources in the face of recent deleterious events such as climate change, Covid-19, hurricanes and other natural hazard impacts, and global economic crises, among other challenges, should nudge many developing countries toward the application of Fit for Purpose Land Administration (FFPLA) as opposed to costly and lengthy standard methods. Problems arise in convincing states of the benefits of applying the FFPLA. This paper explores how fit-for-purpose methods for establishing and upgrading land administration infrastructures have become increasingly imperative to developing countries, particularly small island developing states (SIDS) of the Caribbean, in light of declining economies. The experiences of Caribbean countries, with a focus on Trinidad and Tobago, Barbados, Saint Lucia, and Jamaica, in implementing adjudication and titling for their land administration, are compared to FFPLA guidelines in terms of major objectives, supportive legislation, and method of application. Based on the outcomes of the evaluation, it is suggested that including more facets of the FFPLA, primarily for progressing the process toward economically beneficial success, would be an advantage.