California’s reentry system is fundamentally broken, not because people don’t want to succeed, but because we expect success without structure. Probation and parole rely heavily on personal accountability, yet operate on what amounts to an outdated honor system with minimal technological support. This approach is both inefficient and unrealistic. Without effective monitoring and wraparound support, individuals are left to navigate housing, employment, healthcare, and legal obligations alone, often setting them up to fail. Leveraging technology to provide real-time monitoring, guidance, and personalized support isn’t just smart, it’s necessary. When done right, these tools can dramatically reduce recidivism, promote accountability, and create clear pathways to long-term stability.