In 2006 Inland Revenue claimed Tannadyce Investments - a company Henderson was the sole director and shareholder of - owed income tax of $356,686.79.
In 2008, the IRD issued a statutory demand for the tax said to be owed. But Henderson said IRD was deliberately withholding documents that he needed to prepare tax returns.
Although the time in which Tannadyce could file a challenge to the demand had expired, the firm argued it could file judicial review proceedings to have the assessments quashed.
A judicial review is an examination by the High Court as to whether a decision made by a public body has been made lawfully. When the Christchurch High Court dismissed Tannadyce's application against the demand, Henderson took the issue to the Court of Appeal.
It found Tannadyce "had no arguable basis to dispute the liability for the sum claimed in the statutory demand".
When the issue was taken to the Supreme Court, Tannadyce failed again. In a decision released yesterday, Supreme Court Justices Dame Sian Elias, John McGrath, Thomas Gault, Peter Blanchard and Andrew Tipping upheld the decision to strike out the application for judicial review.
Speaking to the Herald yesterday, Henderson said he still could not access the documents allegedly held by the IRD.
"We're stuffed. The Supreme Court is the end of the line."