The transition to school is a time of change and expectation for children, families, and communities. It is also a time when a range of factors--both within and outside the family--influence educational experiences and outcomes. This paper reports the experiences and expectations of 24 Australian families as their children with special needs started school. Life for these families was complicated by their experiences of other factors described as complex support needs. Drawing on interview and case study data, we report issues and concerns, and examine the supports available for these families and their children across the transition to school. In analysing the data, we consider the ways in which children's special needs interact with the complex support needs of families, and consider implications of this interaction as families navigate access to support. We conclude that this interplay positions many families in ways that reinforce, rather than reduce, the difficulties encountered.