Adrian Chiles is set to face a fourth tribunal hearing as part of a £1.7mn tax battle with HM Revenue and Customs which has been ongoing for 10 years.
A judge initially ruled in favour of the broadcaster in 2022, but earlier this year it was revealed legal errors had been made meaning the case should now be heard again in the First Tier Tribunal.
The case related to Chiles' company Basic Broadcasting Ltd and two bills issued by HMRC, which totalled £1,249,433 and £460,739, under IR35 rules applicable to off-payroll contractors.
The bills were for work done at the BBC and ITV between 2012 and 2017.
Dave Chaplin, CEO of IR35 tax advisory firm IR35 Shield, said: "Parliament must take action to simplify the IR35 rules and refine the tax tribunal system to provide greater clarity and fairness for taxpayers.
"Cases like Mr Chiles' serve as a stark reminder of the human cost of this broken system. It's time for meaningful reform to ensure that taxpayers are treated fairly and can resolve their disputes in a timely manner."
A ruling published on June 7 confirmed the case will be heard again in the First Tier Tribunal.
It said: "With reluctance, we have concluded that we should not remake the decision on this issue but should remit it for reconsideration by the FTT."
This is due to what it called an error of law in the successful case in 2022.
Loose Women presenter Kaye Adams had a similar battle with HMRC, which came to a close earlier this year after a decade.
In relation to Chiles' case, she said called it a "costly and stressful exercise".
Adams said: "It seems we are now in a situation whereby HMRC will routinely challenge judgments on the basis of 'errors in law', forcing the taxpayer to foot the bill.
"Despite two rulings in my favour, HMRC took me to the Court of Appeal, apparently to 'get clarification 'on the law, and the upshot was that I won my case again.
"How many times and how many of us have to go through this for HMRC and the tribunal system to get their heads around fair and consistent application of IR35 legislation?"
Seb Maley, CEO of Qdos a IR35 compliance expert, said Chiles faces "another incredibly stressful period" through no fault of his own.
He added: "We see this time and time again. A freelancer proves their innocence only for HMRC to appeal and be granted another hearing. In what is yet another IR35 saga, Adrian Chiles must demonstrate that he is genuinely self-employed once more or face a £1.7mn tax bill.
"It speaks volumes of a system with odds stacked against taxpayers, who can’t move on with their lives just in case HMRC is given another bite at the cherry. The worrying thing is that this all stems from a mistake apparently made by one of the tribunal judges.
