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Streetworkers (SW), also known as violence interrupters and/or credible messengers, are street-level bureaucrats (Lipsky, 1980) who work on the streets of most major cities in the United States. SWs' are part of an inter-agency initiative aimed at intervening in the lives of high-risk youth to reduce gang involvement and gun violence. This study aims to explore the job-related challenges and coping strategies of SWs from their perspectives. Anderson's code of the street theory serves as a theoretical framework to understand the study's findings, which are based on in-depth, semi-structured interviews with 37 SWs from a large city in the United States. SWs reported that the main challenges of their jobs were navigating restrictive policies and bureaucracy, limited funding and support, and a lack of programmatic 'buy-in' from clients. Analyses also reveal that SWs' exposure to violence was an additional challenge. SWs also shared their formal and informal coping strategies to help mitigate these challenges. The findings are discussed using the work of Lipsky and Anderson, and several program and policy recommendations are proposed to improve SW recruitment, retention, job satisfaction, effectiveness, and well-being.