Shoplifter Michael Lowe got his wish when he was jailed for 12 weeks - because he will leave prison with £40.
It was imposed after city magistrates heard he left empty-handed from his last stint inside because it was so short.
Defence solicitor Jo Tait said he was previously sent to prison for four weeks, which meant his release after a fortnight with the rest of the time under probation.
"When it is 14 days, they don't even get their bus fare and nothing to help them survive legitimately," she said. "As a result you find him back before the court.
"He went to a police station, said 'I have committed an offence. Get me back to prison.' His life is better inside than outside - what an indictment.
"Although he is a perpetrator of crime, he is a victim of the criminal justice system and has been homeless with drug issues.
"He has to get himself off this Catch-22 treadmill," said Miss Tait for Lowe, 30, who still has nowhere settled to live.
She said his last prison term had the bonus of getting him off drugs which have been a problem for him since he was 17.
Miss Tait added: "He was released without assistance. He is dyslexic and struggles with forms for claiming benefits."
Lowe admitted twice breaching a Criminal Behaviour Order by entering the Waitrose and Morrison's branches in his home town of Newark. He also pleaded guilty to stealing items worth £40 from Waitrose.
Sanjay Jerath, prosecuting, said Lowe has a criminal record listing 107 offences, including "64 of dishonesty."
Presiding magistrate Andrew Jackson, who sat with two other JPs, told him: "Your solicitor has made clear the difficulties you have been facing every time you come out of prison.
"Nevertheless we have to deal with the matters as prescribed by Parliament. Sentencing guidelines are clear."
Under the latest penalty, he will be inside for six weeks and must pay £115 in government tax. The £40 payment is intended to help former inmates with basics when they are freed.
