Woman jailed after repeatedly shoplifting from stores across Cheltenham
Kayleigh McConnon was sentenced at Cheltenham Magistrates Court
Last updated 19th Feb 2026
A prolific shoplifter has been jailed after CCTV footage showed her repeatedly targeting shops across Cheltenham.
Kayleigh McConnon, aged 37 and of no fixed address, appeared at Cheltenham Magistrates’ Court last Wednesday (11 February) where she was sentenced to 66 weeks in prison after pleading guilty to shoplifting offences.
Officers from the Cheltenham Neighbourhood Policing Team had issued McConnon with a Criminal Behaviour Order in October 2025 after she admitted to stealing perfume sets worth £387 from a shop.
As part of the order, McConnon was banned from entering any retail premise in Cheltenham with the exception of five premises: Tesco Superstore on Colletts Drive, JHoots Pharmacy on Edinburgh Place; Tewkesbury Road Post Office, News Agent on Tennyson Road and Primark on Cheltenham High Street.
Despite being issued with the banning notice, McConnon continued to enter shops and steal items such as food, drinks and clothing.
These reports detailed how McConnon had entered Tesco Express on Hewlett Road on three occasions, stealing several hundred pounds worth of food.
McConnon also entered Superdry clothing and left with a bag full of items of clothing valued at several hundred pounds.
Officers conducted enquiries into the reports and arrested McConnon in connection with the incidents last Tuesday (10 February).
McConnon was subsequently charged with five counts of theft from a shop, five counts of breaching a Criminal Behaviour Order, breach of a suspended breach and three outstanding warrants for her arrest.
She pleaded guilty to all counts and was jailed on the same day.
PC Louis Gilbert from the Cheltenham Neighbourhood Policing team said: "McConnon has been a real problem for local shops and so ensuring she was arrested and charged was a priority for the Cheltenham Neighbourhood Policing team.
"I am pleased that McConnon has been jailed and hope this sentencing shows that retail crime is something we won’t tolerate.
"This court outcome was a team effort and I'd like to thank my colleagues for their support and hard work over recent weeks."