As New South Wales (NSW) bids farewell to the 2009-2014 Area of Study concept "Belonging", this article summarises some critical reflections from English teachers on the main pedagogical issues encountered when using prescribed texts to teach "Belonging" to both the Standard and Advanced English courses in contemporary classrooms. These reflections are convened under three areas for further consideration, which includes an analysis of the Area of Study (NSW Board of Studies English Stage 6 Syllabus), an examination of the prescribed texts listed, and the main challenges teachers have identified with using both the NSW English Stage 6 Syllabus and set prescribed texts to engage contemporary students. The discussions raised in this article can be considered by NSW educators when selecting texts and designing units of work for teaching the new 2015-2020 Area of Study concept "Discovery".