Red pulls a few strings and he, Andy and their friends get the job. Whilst working on it, Andy overhears Hadley (the guard) talking about how he has inherited some money but expects to be taxed heavily on it. Andy approaches the guard and manages to explain how Hadley can keep all the money, despite Hadley's threats of throwing him off the roof for stepping out of line and approaching a guard. In return for this advice, Andy boldly asks if he and his co-workers may have a couple of beers on their last day of work. Hadley agrees and Andy wins many friends. However, he does not drink the beers himself and instead, sits quietly smiling at the sight of his friends being happy. As a result of Andy's advice, all of the guards start coming to him for financial advice and, later, crooked dealings and money laundering. This means that Andy starts to get preferential treatment although 'the Sisters' continue to assault him. After another attack, Andy is beaten within an inch of his life which forces the guards to notice. As retribution for these attacks, Hadley takes it upon himself to punish the ringleader, Boggs. He beats him so severely that Boggs is crippled for life and transferred to a minimum security prison elsewhere. Without Boggs, the rest of the gang are too afraid to touch Andy and his life becomes relatively trouble-free. .
Andy is assigned to work with Brooks, an ageing prisoner who wheels round the library cart handing out books. Andy decides that the library is not big enough and starts petitioning the warden and then the state governors for extra funds. He writes one letter a week for six years before he finally receives a cheque for $200. Andy feels this is insufficient and starts to write two letters a week. Before he receives a reply, Brooks is released having served a sentence of fifty years. The film follows him into the outside world which he finds terribly frightening and lonely.