Second chance education programs are now a well-established presence in institutions seeking to provide access and equity pathways for socio-economically disadvantaged groups. This paper focusses on the strategies used to support positive engagement in second chance equity programs, drawing upon evaluation research data from four TAFE sponsored programs. Interviews were held with service providers involved in the programs' development and delivery, and focus groups were held to gather information from program participants. The findings highlight the complex and often multiple barriers facing participants and the importance of delivering programs with sustained and tailored approaches. While tangible educational and/or employment outcomes were delivered, it was the associated social and personal development that made these programs especially successful. Hence, there is a need for equity programs to be holistic, scaffolded, and tailored to practical and vocational pathways.