Singapore's education system has often been characterised as exam-oriented. This paper describes efforts ("windmills") made by the Government to constructively respond to the "winds of change" in the education system. A committee called the Primary Education Review and Implementation (PERI) Committee was appointed to study and recommend the priorities, programmes and resources needed to revise primary education in Singapore. The Committee recommended that a balanced school-based assessment system that provides constructive feedback, enabling more meaningful learning in support of both academic and non-academic aspects of a pupil's development, be carried out under the label of "Holistic Assessment". This paper is an attempt at surfacing the challenges ("walls") in implementing "Holistic Assessment" on a large scale, highlighting in particular, the tensions perceived by stakeholders concerning the interaction between formative assessment and accountability systems. It documents how stakeholders, namely teachers and parents, perceive and typify the concept of "Holistic Assessment". The findings provide insights into the consequent realities of a nationwide shift in assessment purpose and discourse on teachers and parents.