Ryan Woodhead claimed to be a milkman and a window cleaner as he attempted to trick vulnerable pensioners into parting with cash.
Woodhead also preyed on the emotions of other victims by lying to them that his grandfather had been taken ill.
Woodhead, 25, was out of prison on licence at the time of his latest crime spree.
He had previously been jailed in 2014 for similar “mean and wicked” offences against the elderly.
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Nigel Wray, prosecuting, described how Woodhead targeted homes across Leeds in December last year and January of this year.
Woodhead knocked on the door of a 92-year-old woman on December 15 and claimed to be collecting milk money.
The pensioner told Woodhead she had already paid her milkman.
Woodhead then took out his mobile phone and pretended to have a conversation with the milkman before telling the victim he needed more cash.
The woman refused and closed the door.
Woodhead tried a similar scam later the same day at the home of an 85-year-old woman, this time claiming to be collecting window cleaning money.
Mr Nassiri said Woodhead managed to persuade an 89-year-old woman in Cross Gates to give him £22 after claiming he was the grandson of her next door neighbour.
Woodhead told the woman his grandfather had been taken ill and he needed to get to hospital to see him.
He returned to the property the same day and attempted to obtain more cash from her.
The victim’s grandson rang police and Woodhead was arrested nearby.
Mr Nassiri said Woodhead had also managed to steal a chequebook from an elderly victim’s home in Bramley on January 19.
Woodhead, now of Lytham Road Preston, pleaded guilty to six offences of fraud and one of theft.
He was jailed for 18 months.
Stephen Smithson, mitigating, said Woodhead had pleaded guilty to the offences at an early stage.
Jailing Woodhead, Recorder Sophie Drake said: “You embarked on a campaign of fraud targeting elderly people to try to get money out of them.
“You pretended to be somebody else or preyed on their emotions.”
**Woodhead was jailed in August 2014 after he targeted vulnerable care home residents in the Beeston and Holbeck areas of Leeds.
One victim was conned into handing over cash after he was told he had won a raffle prize.
Woodhead also claimed to be a police officer when he preyed on a 79-year-old man who had previously been the victim of a burglary