This paper describes the processes involved in exploring the ‘lived reality’ of one group of Year 6 rural students as they made their transition to high school. A range of qualitative data collection techniques were used to track the experiences of the students during their last few weeks of primary school, and their transition to high school. Using the principles of Grounded Theory and specifically the processes of constant-comparative analysis, three categories emerged: Adaptation to Organisational Culture, Adaptation to Social Culture and Personal Reactions and Adaptations. While the transition to high school for the rural students was an eagerly anticipated event, the students also held many anxieties relating to the ‘Organisational Culture’ of high school. For example, some of the students reported that it was difficult to find their way around the high school. The ‘Social Culture’ of the high school was also a concern for the rural students, particularly due to the possibility of not having friends and being vulnerable to older students. These feelings continued during the students’ initial weeks of high school but were later replaced by a focus upon academic requirements and the changing nature of social friendships. The third area of concern, ‘Personal Reactions and Adaptations’, related to how students responded differentially to their transition. Recommendations based upon these findings focus upon initiatives that may promote a smooth transition and can be accessed and implemented by both primary and secondary schools and students.