AI-Powered
Reentry
A vision for the City of New York and the Department of Correction: an adaptive reentry and work-readiness system supporting the transition from custody to community.
This is not a course about artificial intelligence. It is an AI-powered reentry system that personalizes education, work readiness, and transition planning from custody to community.
The Problem
People leave custody into a world that has changed while they were away. No single fixed curriculum can serve people starting from such different points.
One participant may have been in custody for three months; another for several years. Some are ready to learn modern digital and AI tools. Others first need support with passwords, email, online applications, resumes, banking, government services, identity documents, and protecting personal information. For them, the first barrier is not a lack of AI knowledge — it is the missing infrastructure of modern life.
An adaptive AI system can assess each participant’s starting point and build an individualized learning and transition plan, without requiring staff to design a separate curriculum for every person.
Lengths of stay and release dates are highly variable, and a traditional linear curriculum is not well suited to this environment.
The Core Idea
The question is not “how do we teach people in custody to use AI.” It is: how can AI help participants build reentry readiness, navigate today’s digital and working world, develop marketable skills aligned with employer demand, and reduce the likelihood of returning to custody.
An adaptive learning engine
Personalizes content, pacing, and support — the participant experiences a program built for them, not a menu of settings.
A working tool
Accelerates the path to entry-level job readiness on real, employer-relevant tasks.
Briefly, a subject of study
Enough literacy to use AI safely and well — not a specialization.
We deliberately do not promise to turn participants into “AI specialists.” AI alone is not a profession; it becomes valuable when applied to a specific occupational function tied to real employer demand.
The Participant Journey
One plan, assembled per person: from an individualized assessment to demonstrated skills an employer can evaluate, and a transition plan that continues after release.
- 01Assessment
Individualized assessment, not a test
The program begins with a short adaptive conversation and practical tasks that assess literacy, digital literacy, work history, interests, and the time likely available for participation. The result is an individualized learning and transition plan: two participants on the same platform may follow completely different programs. The system does not replace educators, program staff, or Transition Coordinators; it gives them the ability to deliver individualized support at a scale that would otherwise be difficult to achieve.
- 02Access
An interface that adapts too
Plain-language, voice-supported, multilingual, and accessible to participants with limited literacy, limited digital experience, or disabilities.
- 03Layer I
Digital literacy and foundational life skills
Builds the skills needed for daily life and successful reentry. Participants move past skills they have already demonstrated and receive support where needed.
DevicesEmailPasswords & account securityOnline formsResumes & applicationsBankingGovernment servicesIdentity documents (IDNYC, SSN)Scam recognitionPersonal-data safety - 04Layer II
Personal agency, self-regulation, and work readiness
The spine of the program is personal agency: the ability to make intentional decisions, set goals, and follow through on commitments. This layer builds emotional regulation, goal-setting, accountability, and recognition of patterns that may interfere with progress — drawing on mindfulness and leadership programming already delivered at Rikers Island, in a secular format. On top of it come work-readiness skills: professional communication, conflict management, receiving and applying feedback, and job-interview preparation — trained through scenario-based AI simulations that adapt to the participant’s responses.
- 05Layer III
Practical AI literacy
A brief, task-based module: what AI can and cannot do, its limitations and likely errors, how to verify its outputs, what information should not be entered into an AI system, and how to give clear instructions and evaluate results. Engagement comes from completing a useful real-world task, not from learning terminology.
- 06Layer IV
AI-enabled career pathways
The platform guides each participant toward one of five to ten AI-enabled entry-level roles — functions where AI can accelerate skill development and support entry-level job readiness. Each pathway will be co-designed and validated with employers, beginning with the real tasks they need entry-level employees to perform.
T01Administrative and paperwork supportT02Customer supportT03Data entry and operationsT04Bookkeeping supportT05Content productionT06Scheduling and coordinationT07Research and documentation supportWith the right preparation, a participant is better equipped to contribute during the first weeks of an entry-level job. - 07Evidence
Demonstrated skills and recognized credentials
Each pathway produces a portfolio combining demonstrated competencies, verified work samples, and relevant certificates. Rather than course completion alone, an employer can review what the participant has actually done.
What an employer can review- Processing a customer inquiry
- Drafting a professional response
- Entering information into a system
- Recognizing when to escalate
- Verifying AI-generated output before it is used
- 08Placement
A bridge to employment
With the participant’s consent, verified work can be shared with participating employers, who can identify candidates by demonstrated skills rather than by credentials alone. Interview and early-employment feedback flows back into the program, so pathways reflect what employers actually need.
- 09Continuity
Transition planning support
Learning is converted into concrete inputs to the participant’s transition plan: documents to obtain, appointments to keep, applications to complete, and next steps toward employment. The system is designed to support — not duplicate — the work of Transition Coordinators and community-based providers: it maintains the information they rely on, tracks tasks and deadlines with clear owners, and surfaces what has not happened. Referrals and services remain with the providers; the system records confirmation and keeps the participant on track between appointments. When a participant transfers or is released, the learning record and transition plan move with them and continue on a personal mobile device.
Support for DOC Staff and Providers
The system flags needs that require timely follow-up; it does not make decisions.
Less reconstruction, more contact
Authorized staff see each participant’s progress, key gaps, participation and engagement indicators, and progress toward individualized transition goals — more time with the people who need attention now.
Aggregated reporting
Participation, completion, skill attainment, work readiness, employment outcomes and, over time, agreed-upon return-to-custody measures. Program staff access only the individual information needed to support a participant.
Not a surveillance tool
Individual data is not used for disciplinary decisions, custody classification, release or legal decisions, risk assessment, or profiling, and the educational record is kept separate from a person’s criminal case.
Security and Governance
The product is designed for correctional environments from day one — including existing tablet infrastructure and facility rules — and can operate through either of two deployment models.
Closed, locally hosted
- Local deployment
- Curated knowledge base
- No open internet access
- Comprehensive audit logging
Controlled-access connected
- Approved models only
- Filtered, logged gateway
- Data minimization
- Comprehensive audit logging
- Minimal data collection
- Role-based access
- Full audit of system activity
- No employer or partner access without participant consent
Educational content is approved, version-controlled, and grounded in curated sources. Sensitive guidance — legal, financial, medical — is reviewed with qualified program partners, uncertain answers are escalated to staff, and quality, bias, and error rates are continuously monitored.
What the City Gets
A reentry program that is measurable by design. Program components are continuously evaluated against agreed measures, and components that do not demonstrate value are revised or discontinued.
| Metric | Measurement window | Definition of success |
|---|---|---|
| Recidivism outcome | 3 / 6 / 12 / 24 months | Definition and comparison method agreed before the pilot |
| Employment after release | Within 90 days | Placement confirmed |
| Job retention | 6 and 12 months | Retention tracked |
| Reentry stabilization | Continuous | ID documents, housing stability, public benefits, kept appointments |
The specific recidivism outcome — rearrest, reconviction, reincarceration, or return to DOC custody — and the comparison method will be defined jointly before the pilot begins.
Beyond the numbers: a program that extends the reach of existing staff and community-based providers rather than replacing them; continuity that survives transfers and continues after release; and results supported by transparent, agreed-upon measures.
How a Pilot Would Run
One facility, a limited voluntary cohort, and success metrics agreed before the pilot starts.
- One facility
- A limited, voluntary cohort
- A designated staff liaison
- A security and technical review of the two proposed deployment models
- Success metrics agreed before the pilot starts
- The staff dashboard from day one
- Regular reporting
- Minimal operational disruption to existing programming
- Integration with existing education and reentry programming
- Interoperability with transition planning by contracted providers
Stakeholder interviews and review of the existing tablet infrastructure.
One facility, voluntary cohort, staff dashboard live from day one.
Measured against the metrics agreed before the start.
Expansion decided together, on evidence.
Who We Are
The team combines years of direct program delivery at Rikers Island — mindfulness and leadership programming, with established relationships with people in custody, facility staff, and DOC leadership — and experienced product and technology leadership.
The program will be co-designed with community-based reentry providers and employers from the start.
Next Steps
- 01
A working session with the administration and the Department of Correction to align on goals, constraints, and security requirements.
- 02
Access to conduct an initial needs assessment and co-design phase: stakeholder interviews and review of the existing tablet infrastructure.
- 03
Jointly define a limited pilot in one facility, with target population, implementation requirements, and success metrics agreed in advance.
Not a completed lesson or a certificate. A changed life trajectory: a person who leaves custody understanding the world they are entering, knowing what work they can do, able to get and keep that work — and not returning to custody.