Sylvia Marquiss, 58, manipulated her victims by telling them she was seriously ill and avoided paying for rent, bills and expensive jewellery, Truro Crown Court heard.
Some were left distressed and "saddled with debt", the court heard.
She was sentenced to two and a half years in jail.
Mrs Marquiss, of Falmouth Road Truro, pleaded guilty to four counts of fraud committed around Cornwall in 2014 and 2015 but "showed no regret whatsoever", the judge said.
Judge Christopher Harvey Clark QC highlighted that she had several previous convictions around the country for "despicable" frauds where she had also conned friends out of thousands of pounds by pretending she was terminally ill to gain their sympathy.
In one case in Cornwall she "concocted a web of lies" to an old school friend claiming she had an eye tumour so she could borrow ??3,000 - but when the friend asked for the money back Mrs Marquiss instructed a solicitor to write back to her telling her it amounted to harassment.
In another case she moved into a luxury home in Polperro and claimed she needed triple bypass surgery, accruing rent arrears of ??8,000. She then threatened a restraining order when the landlady pursued the money she was owed.
The prosecution said this had left the victim "saddled with significant debts."
Sylvia Marquiss also conned a jeweller in Liskeard into letting her leave a shop with rings worth ??10,000 by "building their trust" and telling them she was suffering from a brain tumour.
They made an exception for her to pay by cheque, which bounced as she had ??1.24 in the account.
"You have committed flagrant dishonesty" Judge Harvey Clark told her.
"You are a heartless rogue and this time you will receive your comeuppance," he said, sentencing her to 30 months in prison.
A "heartless rogue" has been jailed for repeatedly lying about having cancer to defraud friends and businesses out of several thousands of pounds.