Adam Elliott, 37, climbed into the vehicle as the owner and two local residents were trying to jump start it in Deepdale Court, Stoneyford Road, Sutton-in-Ashfield.
Witnesses described how he franticly searched for the keys before being disturbed by the dog on the back seat
After jumping from the vehicle on the evening of December 28 last year he then turned his attention to the person who was helping to jump start the car and his girlfriend – grabbing hold of her and demanding money.
Elliot, who’d only been released from prison around two weeks before, fled on a stolen bicycle after being given a small amount of loose change by the partner of the female at the scene.
He was arrested by police shortly afterwards and taken into custody.
He later pleaded guilty to one count of robbery, two counts of attempted robbery and one of possession of cannabis.
Appearing at Nottingham Crown Court on Thursday, Elliot, of Scargill Walk, Eastwood, was jailed a total of three years and four months.
An additional charge of being in possession of a bladed article will remain on file.
Detective Constable Tim Baker, of Nottinghamshire Police, said: “This was an incredibly frightening experience for the victims and I commend them for their bravery in coming forward and giving evidence in this case. Incidents like this can leave lasting emotional impact and I hope they receive some degree of comfort from this sentence.
“Elliott is a violent and repeat offender who thought he could simply take the money he wanted from wholly innocent bystanders. This kind of brazen thuggery will always generate a very forceful police response and – as Elliott has just found out – often end in a prison sentence.
“I hope this case serves as a strong warning to others about what will happen if they also commit these kind of offences.”
*Elliott pictured with injuries’ sustained prior to this incident.