Incarceration in the United States has reached unprecedented proportions. While a number of studies have found evidence for independent effects of incarceration on indicators of well-being, such as mental health, some of these also precede criminal behavior and subsequent incarceration. Education is one such attribute that can be both a predictor and an outcome of incarceration. Yet vast majority of research has focused on education as a precursor to incarceration, with very little attention paid to the possibility of reverse effects. We know, for instance, that young men who have dropped out of high school are at a dramatically high risk of becoming incarcerated but we know comparatively little about the role that incarceration plays in decreasing or increasing educational attainment. In this paper, we examine the effects of incarceration on attaining high school qualifications among current and former inmates. We use the National Longitudinal Survey of Youth 1997, a panel study that follows a nationally representative cohort of nearly 9000 participants. There are 14 waves of data currently available. Most important for our purposes, the data include detailed measures of contact with the criminal justice system and educational experiences, as well as a variety of correlates of both. Having rich measures and longitudinal data is critical for studying the effects of incarceration because of the formidable methodological challenges with respect to selection bias. Building on the advantages of panel data, we use propensity score analysis to create a rigorous study design by matching participants who have been incarcerated to those who were incarcerated later in life. We expect that having been incarcerated will decrease the odds of completing high school, but remain open for the possibility that incarceration may have a positive effect on educational persistence and attainment.