Numerous studies have examined the influence of offender characteristics on sentencing outcomes, yet little attention has been afforded to offenders’ educational attainment. The focal concerns theory provides reason to suspect that greater educational attainment may insulate offenders from the effects of criminal stereotypes linked to extralegal factors, including race/ethnicity, age, and sex. The current analysis employs a sample of 115,674 federal offenders to test this assumption on the in/out and sentence length decisions. Results of the in/out models demonstrate a general pattern where the effects of several extralegal factors (i.e., race, ethnicity, age, sex, and detention) are reduced, and in some cases fully moderated, by offenders’ educational attainment. This pattern, however, is not apparent during the sentence length decision.