A man visited The Mount jail in Bovingdon intending to swap trainers with an inmate so he could smuggle drugs to him.
But a prison officer had already spotted Jake Bailey, 23, handing over a package to the man and was caught before he had a chance to exchange shoes.
Today/Friday Bailey, of no fixed address, was jailed for 2 years after admitting conveying a prohibited item into prison, supplying cannabis and synthetic cannabis and possessing pepper spray.
Prosecutor Daniel Siong said 66 grams of cannabis and 88 grams of synthetic cannabis were recovered along with the pepper spray from the car that Bailey arrived in.
He said: “The street value of the drugs is £1550, but in prison it is 5 to 10 times that amount.”
The prosecutor said: “Mr Bailey was observed by a prison officer as he handed over a package.
“He was not being discreet. He was found to be wearing a size 8 trainer with drugs and it is suspected he was going to swap shoes.”
Defending, Daniel Robinson said Bailey was homeless, having been kicked out by his parents because of his use of cannabis. “He was living in a tent or staying with friends. He was homeless and struggling with addiction.”
At the Mount, he said: “He was not being discreet when passing drugs and did it very badly.” He did it because he was in debt to dealers, the court was told.
Jailing him, Judge Nic Madge said: “Drugs are a form of currency in prison and can have an effect on prison discipline.”