A bereaved man claims he was forced to pay £3,000 after Birmingham City Council pursued him for a Clean Air Zone fine incurred by his late father.
Gary Davies told the BBC he felt like an "absolute loser" after he was unable to convince the local authority his father had died.
The 52-year-old roofer said trying to get through to someone to argue his case had been like "talking to a brick wall" and he would now take legal action against bosses.
The council defended its administration of the scheme and said opportunities for challenge were very clearly set out.
The zone was launched in 2021 as part of plans to tackle poor air quality and introduced daily fees for older vehicles driving in the city centre.
A report in January found it had made a "significant" contribution to reducing pollution.
But in the years since its introduction, it has been repeatedly criticised as seemingly innocent people face thousands of pounds in fines.
Others have said it is difficult to get in touch with the local authority to dispute charges, and claimed the council has been unwilling to listen.
Mr Davies, from Tamworth, Staffordshire, explained he had to hand over £3,000 when enforcement agents clamped two vehicles outside of his property.
He is yet to get his money back despite supplying a copy of his father's death certificate, and said the ordeal had made grieving more difficult.
"I was on the phone for two-and-a-half hours one day trying to speak to somebody," he said.
"It makes you feel like you're an absolute loser because nobody will listen to you."
