In this paper we consider the importance of student self-assessment in classrooms where teachers are working towards real, powerful and enduring levels of student engagement. Here student engagement is defined and characterised by students becoming fully involved as 'insiders' in the learning culture of their classrooms. How to recognise this level of engagement and bringing the students into the 'insider' culture needs careful consideration. The paper draws on current research in the Fair Go Project. This research in a Priority Schools Funding Program (PSFP) school is investigating ways that teachers can support students in processes of reflection and evaluation of their own learning. This support is concentrating on self-assessment probes that bring together affective and cognitive reflections in a process of increasing intellectual challenges. The suggestion here is that student engagement is most likely to be found when there are high levels of both feeling and thinking. Student self-assessment is recognised world wide as an interesting and vital way for children to learn. Through self-assessment they can more fully understand both the content and processes of their learning. As well, a focus on student self-assessment can provide a powerful impetus on important changes to the learning culture of classrooms. While it is well documented that self-assessment is beneficial to both the students and the teachers (Bryant & Timmins, 2003; Hart, 1999; Black & William 1998), not a lot has been done that takes self-assessment beyond reflection on what was learnt and what was liked to a higher level of intellectual quality and student engagement. As a response to this need the research reported in this paper has developed a multi-dimensional reflective framework to promote deeper student reflections about learning and critical changes to teachers' pedagogies.