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Jeremy Leith Gray, 45, fronted Levin District Court in New Zealand 's lower North Island this week.
Police arrested the vagrant after he was caught shuffling down a busy road and dodging oncoming cars.
Drivers were forced to swerve around Gray as he pushed his trolley.
To avoid a repeat situation and raise his visibility, Judge Sygrove suggested in court that Gray install an LED light onto his trolley.
He said the LED light meant Gray wouldn't need to keep buying batteries.
'You must keep off the road,' Judge Sygrove told Gray in court, NZ Herald reported.
Judge Sygrove's suggestion came as Gray's lawyer Kelvin Campbell told the court his repentant client would take more care in the future to not wander onto the road.
Gray had also promised to use a light on the trolley.
Social media users have since taken to Facebook to comment on the judge's suggestion.
'Next he will need to take it [trolley] and get a rego,' one user said.
'Someone give that man a Hi-Vis ... judge offer to pay?' another commented.
Gray is reported to have been wandering the streets for years, and to have also previously faced court for a separate matter.
Authorities found Gray squatting in an empty property on Bryant Street at Palmerston North, about a 40 minute drive north from Levin back in 2013, Stuff reported.
At the time he was charged with being unlawfully in a building and even faced a prison sentence if he could not find a place to live.
His then-defence lawyer Jock Turnbull told the court Gray had always wanted to live on the streets.
This time around, lawyer Mr Campbell said that Gray had a concerned and caring family member living at Foxton Beach along the east coast of the island.
He noted that was always an optional living arrangement for Gray.
Gray was sentenced to reappear in court if called upon in the next 12 months.
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