In 2023, he was arrested in Chicago for a stolen vehicle case, which was later dismissed. Osama served 14 months in federal prison for the New York gun charge, receiving a lenient sentence due to his clean record. Lil Zay Osama discussed his experiences with violence and survival in Chicago, including being shot at 15 and moving out of the city two years ago. He announced his final drill tape and mentioned his recent baptism and his transition to independence after seven years with Warner Bros. The conversation also touched on the impact of violence on artists like Bloodhound Q50 and the challenges of maintaining peace in the drill scene.