Nick Hudobenko is a Correctional Officer and Correctional Counselor for the Connecticut Department of Correction. He also works with the DOC Offender Re-Entry Services Unit to help find jobs for inmates who are finishing their sentences. Prior to working with the DOC, Hudobenko was in the United States Army National Guard and worked as a Military Police Squad Leader. He received a Master's in social work from UCONN and a Bachelor of Science from Charter Oak State College. We discussed the difficulties of regulating COVID in a confined space, the work that needs to be done in society to accept those with criminal backgrounds, increased anxiety for those facing re-entry in the pandemic, and keeping inmates motivated.