Emails obtained in this process were claimed by the Official Assignee to contain evidence Henderson was managing a company while bankrupt, and were forwarded again to an investigator with the Official Assignee's National Enforcement Unit.
Henderson was finally released from bankruptcy in January following a public examination by the Official Assignee, but subjected to an additional six-year ban on managing a business.
Justice Hinton noted his bankruptcy was "complex and challenging", given Henderson was involved with up to 100 companies and two trusts.
Henderson complained that the Official Assignee obtained the files through an overly-broad request for information, and also failed to properly safeguard his privacy by not screening out - and continuing to hold - material of a purely personal nature.
Justice Hinton said the prescribed powers of the Official Assignee to seize documents "would not extend to personal documents that are clearly irrelevant to the bankruptcy".
She declared the request for information from the Official Assignee to the liquidator to be unlawful, and also it should not have continued to retain material irrelevant to its investigation.
"The Official Assignee needed to make a requisition using either the language of the section, or listing categories of documents ... or a combination of the two," the judgment said.
Henderson had sought damages of $20,000 in the case, to "recognise his loss of dignity" but Justice Hinton declined to made any such award and said she would only make a declaration the breach had occurred.
"While an important right has been breached, the extent of the breach was not great ... It is difficult to say that there was any significant degree of harm to Mr Henderson." Justice Hinton said.
Henderson was bankrupted in November 2010.
Associate Judge Robert Osborne last year estimated the total indebtedness of Henderson's bankrupt estate "as falling somewhere in the range of $100 million to $150 million".
Henderson is appealing that judgment and disputes that figure. He said evidence was not produced to support it.
He also said that tens of millions of dollars of debt was repaid through sales of property and settlements.