Much has been written about the deputyship regime in Singapore and the operation of the Mental Capacity Act 2008 (MCA) in relation to it. In addition, there are also articles on the pertinent issue of capacity assessments and writing of medical reports for deputy applications. In reality, however, there remains a significant gap in the understanding on how theory and practice meet in the area of capacity assessment and a desire for a more grounded approach towards implementing the framework set out in the MCA for capacity assessment. In particular, there is difficulty in setting the threshold of understanding required in the functional component of the test. This article aims to provide some user-friendly guidance that can be adopted in capacity assessments and a practical explanation on how we can ensure that capacity assessments are as robust and accurate as they can be. While doing so, I hope to encourage and catalyst the evolvement of a group of capacity assessors who can meet the demands and increased sophistication of how we preserve and enable autonomy, and to assist professionals, in particular doctors and lawyers, to cooperate with each other when an cross-disciplinary approach is required.