Over the past 30 years, the U.S. inmate population has increased dramatically, and the penal system has acquired growing attention in accounts of recent trends in economic stratification. As the prison system has expanded, its population has aged; incarceration rates have risen sharpest among older age groups. A large body of research documents differences in criminal offending and incarceration over the life course, but little attention has been paid to how the effects of spending time in prison depend on the timing of incarceration in the life course. Using state administrative data that provide significant variance in the age of offenders, this article investigates how the timing of incarceration in the life course influences its effects on post-release employment and wages. We do not find consistent evidence that incarceration effects vary by age at admission. Instead, incarceration appears to have important consequences for employment and wage outcomes regardless of when individuals are admitted to prison. Even the most motivated offenders suffer sizeable and significant wage penalties and, over time, decreased likelihood of employment. These findings underscore the relevance of legal and institutional shifts associated with carceral expansion and the aging of the inmate population for life course theories of criminal desistance, accounts of labor market inequality, and prisoner reentry programs.