Three men have been jailed for a total of more than 18 years for terrifying masked raids involving betting shops, a rural post office and a jewellers.
Mainly small amounts of cash were stolen from Corals in Tovil, Borough Green and Rochester; Betfred in Larkfield; and Ladbrokes in Snodland.
Cigarettes were taken from a post office in Grafty Green, a robbery was bungled at a jewellers in Ramsgate and violence was used in a car-jacking in Medway.
Jack Hennessy, 27, was jailed for eight years
Jack Hennessy, of Pollyfield Close, Snodland, was handed the longest sentence of eight years.
Keith Hodgson, of Holborough Road, Snodland, was jailed for six years and eight months and Peter Taylor, 21, of Queenborough Road, Halfway, for three years and eight months.
Hennessy, 27, and 32-year-old Hodgson admitted conspiracy to rob and possessing a machete.
Taylor, who admitted one robbery, is currently serving a four-and-a-half year sentence for ram raids and the latest sentence runs consecutively.
Keith Hodgson, 32, was jailed for six years and eight months
Maidstone Crown Court heard muscular Hennessy was identified by distinctive underpants caught on CCTV and footprints left behind when leaping over the counter at some of the betting shops.
The raids took place between November 28 and December 16 last year.
Prosecutor Anthony Prosser said £934 was stolen from Corals in Tovil, £462 from Corals in Rochester, £275 from Corals in Borough Green, £310 from Betfred in Larkfield and £230 from Ladbrokes in Snodland.
Cigarettes worth £1,500 and vodka were snatched from Grafty Green post office and stores in Headcorn Road where postmistress Rosemary Smith bravely refused to cooperate.
Peter Taylor, 21, was jailed for 44 months
Stephen Ruffle was beaten up in a car park in Rochester on December 4 as the gang stole his Seat Ibiza to use for further crimes.
Quick-thinking staff foiled the raid on Cuttings Jewellers in Queen Street, Ramsgate, after three men burst in brandishing a machete on December 16 and one shouted "Get the Rolys" in a reference to expensive Rolex watches.
A member of staff shouted "Press the fog" and the shop was immediately filled with thick smoke making it impossible to see. The robbers left empty-handed.
Judge Charles Macdonald QC accepted there was genuine remorse, but added: "Inevitably, you are all going to prison."
A CCTV image released by police after the raid at Ladbrokes in Snodland
John Fitzgerald, for Hennessy, said it was relatively low-level robbery down to nothing being stolen.
Disguises were basic, a weapon was used only to threaten and there were no injuries in the main raids.
"He ended up in the prison system at a young age," said Mr Sinclair. "He found himself with others far more sophisticated in Belmarsh.
"He looks older because of the ravages of addiction. I am afraid he has fallen into bad company..." - Philip Sinclair, for Keith Hodgson
"He intends to embrace the sentence. His mother has a business in Spain. He has taken courses in prison and wants to become a personal trainer."
Philip Sinclair, for Hodgson, said the father of a two-year-old child was motivated to commit the offences by his spiral into drug addiction.
"He has a lamentable record which began when he was 18," he said. "He is now 32. He looks older because of the ravages of addiction. I am afraid he has fallen into bad company."
Taylor was serving another sentence in prison when he asked to see the police to confess to the post office robbery, said his lawyer Fergus Malone.
Rosemary Smith, who was working alone, "plainly stood up for herself", Mr Malone added.
Stories you might have missed