The embattled music moguls bid for an early release from prison gained some momentum nov. How long will diddy stay on supervised release? During combs’ five years of supervised release, the bad boy records founder will be barred from. How long did diddy go to prison? · sean diddy combs is appealing his conviction and sentence — heres an explainer of everything you need to know about the case and his arguments. · sean diddy combs may have a new legal home, but his eye remains on freedom. What will diddy do after he leaves prison? · according to court filings obtained by our friends at tmz, once diddy leaves prison , he will be under close supervision and must follow several conditions set by the court. 3 after a judge signed. · diddy will remain on supervised release for five years after he finishes his four-year sentence. · diddy begged an appeals court to free him from fort dix for christmas, arguing his 50-month sentence ignored the jury’s not-guilty verdict. Mere days after diddy was moved to a low security facility in new jersey, a federal appeals judge today granted the request of the grammy winner’s defense team to expedite the process. The music mogul could regain his freedom sooner rather than later, based on several factors, including. · although the bop shared a potential release date for diddy , the outcome wasnt set in stone. Is diddy a perversion of justice?