To help individuals successfully reenter society after time in jail, the U.S. Department of Labor (DOL) awarded $10 million in grants to 20 local workforce development boards (LWDBs) in June 2015 for the Linking to Employment Activities Pre-Release (LEAP) initiative. Central to the LEAP initiative was creating jail-based American Job Centers (AJCs) with direct linkages to community-based AJCs. A complex array of factors including jail and local community characteristics influenced the development and operations of jail-based AJCs as well as the experiences and outcomes of participants. The overarching goals were to increase participants’ work readiness at the time of release, increase employment after release, and reduce recidivism; additional goals for the pilot initiative included demonstrating that corrections and workforce agencies could effectively collaborate to provide pre-release services, generate lessons learned around promising strategies and common challenges that could inform future efforts; and identify ways for grantees to sustain the jail-based AJCs when the DOL-funded grant ended. The grants covered 9 months of planning and 15 months of service delivery, with many grantees receiving up to a one-year no-cost extension to finish spending down remaining grant resources. Grantees were geographically diverse, located in 13 states across 5 DOL regions, and involved a total of 22 county jails.