Front-end diversion efforts—occurring at initial contact with law enforcement—can prevent overuse of jail custody and the negative impacts that accrue from pretrial detention and acquiring or adding to a criminal record. This case study examines the experiences of Deschutes County, Oregon, and Summit County, Ohio, as they implemented front-end diversion interventions. Practitioners interested in implementing similar efforts can take several lessons from the experiences of Deschutes County and Summit County, including the power of prosecutorial involvement and leadership in the process, the importance of stakeholder support and contribution in early design stages, and a focus on securing and maintaining law enforcement buy-in.