Drawing on eight months of ethnographic fieldwork at a community-based prisoner reentry program, this article investigates how staff members attempt to cultivate former prisoners’ cultural capital to mitigate stigma and facilitate interactions with employers. I call this curriculum work wisdom, which involves teaching clients how to (1) disclose discrediting information and communicate remorse; (2) tailor their style of dress, speech, and bodily comportment to avoid evoking negative stereotypes; (3) negotiate the tacit norms of workplace culture; and (4) remain confident and resilient in the face of rejection. Work wisdom provides former prisoners with the dramaturgical resources to perform dominant cultural scripts and practices in the short term as they undergo the longer-term process of reintegration. These findings illustrate how the cultivation of cultural capital begins by teaching superficial performances that can be internalized as durable dispositions over time. In the conclusion, I discuss the limitations of work wisdom.