In this paper we have applied discrete time survival analysis techniques to analyze education duration in Jamaica. Based on the Jamaica Survey of Living Conditions 2002, we are able to estimate the effects of household, individual, and other related covariates on the risks of students dropping out. We compare the discrete time Cox model and discrete time logit model and determined that the two estimations are consistent. The estimation results measure the effects of the covariates and can be used to predict the dropout risks of particular students in each grade, which could provide useful implications for the formation of policy to improve education in Jamaica.