Addressing school dropout has been one of the most controversial elements of policy since the introduction of free compulsory universal basic education (FCUBE) in Ghana. However, research that utilises qualitative biographical detail surrounding irregular attendance and the critical events in the process that lead to dropout in Ghana is limited. I argue that in order to achieve the target of universal basic education by 2015, education policy should focus more directly on addressing dropout. This paper provides an in-depth analysis of the critical events pupils experience as they cross the threshold from being enrolled to being out of school in southern Ghana. This paper provides fresh insights into drop outs' life worlds and educational needs; opportunities to re-cross the threshold back into basic education, whether into school or complementary provision. The findings presented in this paper show that conditions both external to the school environment--poverty and the opportunity cost of schooling--and within the school--the teacher factor, and school practices and processes--conspire to compromise retention and push and/or pull children out of school.