This guidebook is designed to provide advice from the field to communities interested in pursuing more formal connections--or strengthening existing connections--between the workforce and justice systems. It focuses on specific challenges and how selected communities addressed them. The information was gathered via two surveys and site visits. The first survey asked WIA youth system or Youth Opportunity system representatives to identify the biggest challenges to establishing an ongoing relationship with the juvenile justice system, and to provide guidance from their experiences. The areas covered in this guide were chosen based on these responses. The second survey was then conducted with eight communities--both from within and outside the Communities Collaborating to Reconnect Youth Network--that had experienced some success in addressing these challenges. In six of the communities, site visits were conducted to enable more in-depth gathering of perspectives and information (see Table 1). Several individuals were interviewed at each site, including Workforce Investment Board (WIB) directors, project coordinators, job developers, justice and law enforcement liaisons, youth advocates, and Department of Youth Services staff. The following are appended: (1) Youth Offender Public Management Model; (2) Intensive Aftercare Program Model; (3) List of Resources; and (4) Profiles. (Contains 1 table.) [Funding for this guide also provided by the Jim Casey Foundation.]