Two-Way Stretch, is a 1960 British comedy film, about a group of prisoners who plan to break out of jail, commit a robbery, and then break back into jail again, thus giving them the perfect alibi – that they were behind bars when the robbery occurred. However, their plans are disrupted by the arrival of a strict new Chief Prison Officer.

Plot

Three prisoners nearing the end of their jail sentences, "Dodger" Lane, "Jelly" Knight and "Lennie the Dip", are visited by a vicar seeking to find employment for them. He is actually "Soapy" Stevens, a conman, who proposes a large-scale diamond robbery. They will also all have alibis, because they will break out of prison, commit the robbery and then break back in. With the assistance of Dodger's girlfriend Ethel and Lennie's mother the trio smuggle themselves out in a prison van. The operation is almost foiled by the disciplinarian "Sour" Crout, the new chief prison officer. Everything goes to plan and the trio hide the diamonds in the Governor's office until they are released and can take them away. All goes well until the sack of diamonds is lost on a train. Stevens is recognised and arrested, but the others get away.