Assessment systems reward certainty and thrive on predictability. However, the COVID-19 pandemic has punished our assessment systems severely for over reliance on controlled premises for our high stakes assessment, and this should compel us to re-examine the reliance on certainty and control in our assessment policies and reforms. Singapore is a useful context to examine such re-examination of assessment imperatives on a national scale. The city-state typically orchestrates its major policy reform with great discipline, standardisation, and detailed co-ordination. However, such qualities may not be ideal for its assessment reform needs in the post-pandemic future. Three recent assessment reforms are examined as examples of pre-pandemic assessment policies predicated on certainty. This paper discusses whether such reforms are fit for post-pandemic purpose(s), and argues for shifting the emphasis of assessment from securing examination reliability to developing learners' assessment resilience.