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Singapore is a rapidly ageing society, underpinned by national policies to promote successful and active ageing. Whilst older worker participation in the workforce is encouraged, policymakers are challenged to ensure that work competency is not compromised with any normal age- and/or health-related changes. This paper will briefly outline how policymakers responded to the needs of two subgroups of older workers aged 70 years and above (taxi drivers; crane operators) who desire to continue working in the last two decades. Whilst a mandatory retirement age policy exists for older taxi drivers in Singapore, there is none for older crane operators. Despite this, stricter relicensing protocols were introduced for both types of workers, with active collaboration involving additional occupational therapy services for functional work competency assessments to complement the routine medical fitness screening. Comparisons will be made of these two relicensing frameworks, including the mention of any relevant studies to align with the call of evidence-based practices. In mid-2020, the relicensing policy for older taxi drivers was revised based on findings of a retrospective national database study. Currently, a 4-year national database study on older crane operators aged 70 years and above is being undertaken with preliminary findings to be reported.