A couple who bought and and sold 39 properties - worth $8 million - without paying tax on the profits have lost the latest in a long series of court battles with the IRD.
A ruling in the Court of Appeal said Veena and Yagashwar Singh appeared to be unaware of the need to pay income tax on capital gains from rapid and repeated sales of property.
Profits on such sales have been deemed to be income for decades, even with issues over a possible capital gains tax or the Bright Line Test on investment properties sold within two years.
In the judgement, the court said the value of the sales, between 2002 and 2007, was $8m.
The judges said Mr and Mrs Singh not only failed to meet their tax obligations, but they failed to take advantage of opportunities offered by the IRD to provide a proper disclosure of their transactions.
It said the Singhs' accountant offered to pay $150,000 in 2010, but nothing was done.
A year later, the IRD obtained judgement for tax obligations of $619,730 against Mrs Singh and $574,106 against Mr Singh.
These debts included unpaid income tax, unpaid GST, overpaid family assistance benefits, use-of-money interest and shortfall penalties for gross carelessness.
The couple then offered to make monthly payments of $5000, but after five years, hardly anything was paid.
By 2014, the debt stood at $1.75 million, and the IRD offered to write off most of this on payment of $649,482.
A series of court battles then started, during which the Singhs claimed they were in serious financial hardship, the debt was not payable and they entitled to a tax write off.
The IRD then investigated further and found the Singhs had recently purchased a number of "non-essential items".
They were also not declaring sufficient income to meet their needs.
Bankruptcy proceedings were then set for 2015 - which led to further court action - which found against the Singhs.
The case finally reached the Court of Appeal, which rejected the Singhs application for financial relief.
It then referred the matter back to the High Court to decide how much the Singhs should actually have to pay.
Costs have been awarded against them.