This paper describes a study investigating the professional development of Hong Kong kindergarten teachers. Tracking the teaching and learning of 'play' of six front-line kindergarten teachers by means of the three levels of reflection put forward by Schon (1983, 1987), the study reveals the challenges in the professional lives of these teachers who are working under the conflicting demands and expectations of the society. The result shows that five out of the six informants are entrapped in a 'technicality' of teaching by developing an obsessive hunt for authentic teaching aids. Unfortunately, this behaviour perpetuates under the effect of a self-fulfilling prophecy working within these teachers. Mismatches between the teaching reform and a number of vital core factors for the reform to be succeeded are identified. This paper calls for a due attention to understand the complexities impeding the teaching reform. It echoes the concern of Bascia and Hargreaves (2000) and appeals to policy makers and the public for a fair demand on the role of teachers, who must not be hold accountable for all that is wrong with education, for the scale of the problems that teachers are expected to address just cannot be solved easily by the teachers themselves.