Incarceration has historically been about punishment but recently the trend has shifted towards reform, schooling, and an entrepreneurial spirit. In this report, we look at trends in prison experiences, technology, as well as edtech and entrepreneurship in prisons. Prisons are increasingly enabling inmates to get a vocational training, degrees, and even healing. No longer are inmates looked upon as "less than human" but there is a curiosity about their minds and views that are pro-reform so that they integrate well into society on their release. We then forecast three scenarios on mass incarceration in 2040.