Mark Middleton was on licence after early release from a prison sentence when he struck twice in as many weeks, a judge heard.
The 49-year-old defendant walked into a house on The Broadway in Pelsall through an unlocked door on August 21 and stole a wallet with £100 and a bank card in it, Wolverhampton Crown Court was told.
The 85-year-old occupant, who was alone at the premises, was in the back garden and did not discover the theft until he went back indoors.
Later the same day Middleton used the stolen bank card to purchase £25 worth of food from Nisa stores in Spring Lane, Pelsall and Ablewell Street, Walsall.
Then he saw an 87-year-old woman watering her hanging baskets in Malt House Lane, Great Barr on September 4, started to talk to her and gained her trust by claiming to know her son, revealed Mrs Sati Ruck, prosecuting.
He asked the victim for a glass of water and was invited inside her house where she left him alone in the living room while she went to get the drink which he quickly swallowed and left.
The woman was baffled by what had happened, phoned her daughter for advice and was told to check that her purse had not been stolen. She discovered that it was missing and alerted the police.
The purse contained £10 cash and a bank card which Middleton used within minutes to buy £6.50 worth of food at a nearby branch of Iceland.
Police recognised the culprit from CCTV footage showing his purchases and he was arrested on September 10.
The defendant's previous convictions included 14 distraction dwelling burglaries in which all the victims had been elderly, disclosed Mrs Ruck who concluded: "He deliberately targeted them because of their age."
Mr Exdol Mitchell, defending, conceded: "One could say he was a career burglar and thief but he was in serious financial trouble after his release from his last custodial sentence.
"He was given Universal Credit from which the monthly rent for his probation accommodation was automatically withdrawn."
Middleton from Waddington Avenue, Great Barr admitted the two burglaries and fraudulently using the stolen bank cards.
He was jailed by Judge Michael Challinor who said: "I am satisfied you have been targeting the elderly because you can easily distract and burgle them.
"The homes of people are not safe while you are on the loose so I will confine you for a considerable period."