Peter Reginald Macdonald was locked up for fleecing the state out of more than £40,000 in a four-year period.
He kept secret two cleaning jobs while claiming four kinds of benefits, and took a total of £40,963 from the public purse.
He did not tell the authorities that both he and his wife were working for the same company, Teesside Crown Court heard yesterday.
His largest claim was the £18,477 incapacity benefit for vertigo since September 2007, said prosecutor Martin Towers.
He carried on working during the initial eight-week claim, and handouts continued to be paid.
He was overpaid £16,812 in housing benefit and council tax benefit between 2007 and 2012, £2,911 in income support since July 2010 and £2,761 in jobseeker's allowance during 2007.
In the middle of it all, he ended up in Teesside Magistrates' Court for another benefit fraud.
He was fined for claiming income support and housing benefit without declaring that his wife was working.
This did not deter him, and he continued swindling the state as before.
Macdonald, of Kildare Grove, Redcar, admitted one charge of failing to notify the authorities of a change in circumstances and four of making false representations to obtain benefits.
Andrew Foster, defending, said: "The overpayment has not been used at all to fund any type of lavish lifestyle.
"The overpayments have been used to settle debts, costs and other expenses incurred due to the loss of family members.
Mr Foster said prison would mean the loss of Macdonald and his wife's jobs, loss of support for his wife who was in poor health, and little chance of the money being repaid.
He added Macdonald knew the seriousness of what he'd done and had already paid back £1,600 to the Department for Work and Pensions.
Macdonald had been part of a management team and came to court with references from employers and fellow employees.
Judge Howard Crowson told Macdonald: "Your applications were dishonest from the outset. You were at all times working.
"I'm invited to the view that this is somehow some unhappy situation forced upon you by debt.
"But it seems to me perfectly clear you chose to make dishonest applications.
"This is the sort of offending that is so rife in this country at the moment.
"People seem to contemplate that they can continue these offences safe in the knowledge that they will hardly be detected.
"You chose to spend this money for your own benefit. In this way the country lost £40,000.
"I take the view that it's necessary to send a consistent message about these offences."
He jailed Macdonald for 10 months.
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