Yes, and it is a good sign. What you are describing is exactly how the pre-release phase of work release programs is designed to work. When an inmate is close to their release date, the center gives them structured time outside to look for employment before they walk out permanently. This is typically supervised in the sense that they have to account for their time, check in at set intervals, and return by a designated time, but they move independently rather than with an escort.
The reasoning is sound. Getting a job after incarceration is genuinely hard, and the window between release and employment is when people are most vulnerable to reoffending. Giving someone the chance to line up employment while they still have the structure of a facility behind them dramatically improves the odds of a successful reentry. The inmates who walk out with a job waiting are far less likely to end up back inside than those who are starting from nothing on day one of freedom.
InmateAid also has a free job notification service specifically for people with felony convictions who are preparing to reenter. If your son sends his information and location, the service will text you both with real job openings in his area as they become available through companies that hire people with records. No cost and no obligation, just live leads.