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The Reentry Cliff: Strengthening the Transition from Custody to Community Supervision
SESSION INFO
Monday, August 17, 2026
1:00 PM - 2:30 PM
Session Type: Workshop
The transition from incarceration to the community is one of the most critical—and least structured—periods in the justice system. Individuals face elevated risks of overdose, homelessness, and recidivism within the first days following release, yet coordination across agencies is often fragmented or absent. This session reframes reentry as a systems challenge, rather than an individual failure. Participants will examine where breakdowns occur across custody, pretrial, courts, and supervision—and how gaps in housing, behavioral health, and information continuity undermine outcomes. Through practical frameworks and real-world scenarios, attendees will explore how structured pre-release planning, coordinated workflows, and shared data can create a more effective bridge to the community, improving both public safety and long-term reentry success.
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SESSION PRESENTERS
Robert Ambroselli
Director of Product, Enterprise Supervision, Tyler Technologies
Robert Ambroselli is the director of product for Enterprise Supervision within the Courts and Justice Division of Tyler Technologies, where he leads product strategy, vision, and execution for Tyler’s supervision platform used by county and statewide justice agencies. In his role, Robert partners closely with clients to design and deliver technology solutions that improve case management, streamline operations, and enhance outcomes for justice-involved individuals. With over 35 years of experience in public safety, probation, and parole, Robert brings a practitioner’s perspective to product innovation. Before joining Tyler, he served as Assistant Chief of the Office of Correctional Safety for the State of California and was appointed Director of State Parole by Governor Arnold Schwarzenegger. His deep operational expertise and leadership experience in community corrections inform his approach to developing modern, data-driven tools that support agencies in achieving safer, more efficient supervision practices.
Charles Thomas
Strategic Account Executive, Enterprise Corrections, Tyler Technologies
Charles Thomas has more than 15 years of experience in the Department of Corrections (DOC) space, bringing a strong operational and leadership background to correctional services. He previously served as Vice President of a national commissary company, where he led the planning, implementation, and ongoing support of commissary programs for correctional facility clients. Mr. Thomas managed multidisciplinary teams working both within and in support of correctional institutions, including professionals across IT, warehouse operations, logistics, accounting, and program management. His work focused on ensuring efficient service delivery, maintaining operational integrity, and supporting the unique needs of correctional environments. In addition to his corrections experience, Mr. Thomas holds a Bachelor of Business Administration from the University of La Verne, further supporting his expertise in business operations and management
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