Parents around the globe are increasingly understood to contribute to educational inequality through their choice of schools. This important critique risks minimising the way choice systems may favour certain parents over others. A case study of Singapore and its primary school enrolment process helps illustrate how parent's interactions with school choice systems reinforce some parent's privileges leading to "structure-reinforced privilege." Using a discourse analysis of newspaper coverage and a Singaporean parent website to observe how parents communicate their preferences, we demonstrate that the complex primary enrolment system creates confusion and anxiety among parents, and allows privileged parents to gain an admissions advantage in perceived elite schools. Numerous admission preferences, while initially intended to strengthen family-school ties, rewards those with resources, furthering the perception and reality of economic inequality. The Singaporean primary enrolment case offers ideas for how to simplify school choice systems giving priority to families with limited resources.