"A Retrieved Reformation" opens with Jimmy Valentine working in the prison shoe shop when he receives a pardon letter from the governor. Jimmy meets the news of release with indifference. He has served ten months of a four-year sentence for opening safes, but he had expected to be freed sooner, due to his network of friends outside the prison. The warden lectures Jimmy about how this is an opportunity to become a better man, if only Jimmy can stop opening safes. Jimmy feigns innocence, acting as though he isn't a notorious safecracker.
In poorly fitting prison-issued clothes and shoes, Jimmy walks from the prison to a restaurant to enjoy a satisfying meal. He gives some money to a blind beggar then takes a train to a town where his friend Mike Dolan runs a café. Mike apologizes for not having managed to get Jimmy freed sooner. Jimmy goes to his room above the café and withdraws a dust-covered suitcase full of customized safecracking tools that he himself designed. He returns to Mike Dolan's having changed into a decent outfit and cleaned up his case. Mike asks what Jimmy's plans are; Jimmy acts oblivious as to what Mike might mean, and claims he has a job as a cracker salesman. The response amuses Mike, who pours Jimmy a seltzer and milk since Jimmy never drinks hard alcohol.
News spreads of a string of safe robberies in Richmond, Logansport, and Jefferson City. Ben Price, the detective who arrested Jimmy for the Springfield robbery, takes the case. Ben assumes the thief must be Jimmy Valentine, since Jimmy is the only person with the knowledge and tools to break safes open so cleanly.
Jimmy arrives in a small town called Elmore, Arkansas. He catches the eye of Annabel Adams, the banker's daughter, and falls in love at first sight, immediately foregoing his old life as a safecracker. He settles in Elmore under the name Ralph D. Spencer, opening a shoe shop that soon turns into a profitable business. Over the course of a year, he makes friends and ingratiates himself with Annabel and her family. Two weeks before his wedding to Annabel, Jimmy writes a letter to an old friend named Billy, arranging to give the friend his safecracking tools. He tells the friend he has given up his old ways because of his love for Annabel. Soon after Jimmy sends the letter, Ben Price comes to Elmore.
On the morning when Jimmy plans to travel to Little Rock for the day to give the tools to Billy, Jimmy accompanies Annabel and a few of her family members to the Elmore bank. Mr. Adams shows off the new safe, whose door operates on a clock-release mechanism that can't be opened at any other time. While Annabel's nieces, May and Agatha, are running and playing in the safe, Ben Price enters the bank.
May accidentally shuts Agatha inside the safe. Panic ensues when Mr. Adams says he didn't set the clock and has no way of opening the safe. Annabel implores Jimmy to do something. Knowing that he is about to expose his true identity and lose her love, Jimmy asks Annabel for the rose she is wearing. He then takes off his jacket, shedding his new identity as Ralph D. Spencer and restarting his old identity as Jimmy Valentine. He opens the safe in ten minutes.
Once Agatha is free, Jimmy walks out of the bank, barely registering when Annabel and her family call the name "Ralph." He greets Ben Price at the door and says he is ready to go to prison because his freedom doesn't matter anymore. Strangely, Ben purports not to know what Jimmy is talking about and acts as if Jimmy is actually Ralph Spencer. Ben then turns around and strolls down the street, leaving Jimmy free to live his new life.