Within a climate of continual change this study offers insights into the academic pressures experienced by rural adolescents to achieve at school. In the often challenging transition from childhood to adulthood expectations from others place additional pressures on adolescents' lives. To better understand these pressures, I conducted a qualitative study of six students (ages nine to 15) and their teachers in the Middle Years of Schooling within rural Victoria, Australia. Students were studied prior to the Victorian Certificate of Education (VCE) in order to examine the pressures on students facing the Middle Years of Schooling. The study was carried out over a 6 month period using a Naturalistic Inquiry process with semi-structured interviews and participant observation. This allowed access into the participants' subjective insights. A Collective case study approach was employed to situate the information in its holistic environment and offer thick and information rich narratives depicting the experiences of these early adolescents. The case studies also involved examination of the school experiences of the early adolescents. Academic pressure was then broadly viewed in light of these experiences and recommendations offered. The findings from this research revealed that the early adolescents in the study all experienced degrees of academic pressure and demonstrated varied abilities to cope with these pressures. External support provided by parents, the school, teachers and peers tended to provide support more than fostering resilience.