The Inland Revenue Authority of Singapore (IRAS) invoked its anti-avoidance powers on 124 occasions between 2021 and 2025. Almost every case involved taxpayers extracting profits as tax-exempt dividends or through interest-free shareholder loans.
Two judgments published in June 2026 illustrate how section 33 of the Income Tax Act is being applied by the courts.
Tan Chek Jin Adrian and others v Comptroller of Income Tax
In [Tan Chek Jin Adrian and others v Comptroller of Income Tax \[2026\] SGHC 132](https://www.lawnet.sg), the Singapore High Court considered whether a group of medical professionals had arranged their business affairs with a main purpose of avoiding tax. The precise findings have not been reproduced in the source material, but the case confirms that professional service structures remain firmly in the IRAS's sights.
ZYT v The Comptroller of Income Tax
In [ZYT v The Comptroller of Income Tax \[2026\] SGITBR 3](https://www.lawnet.sg), the Singapore Income Tax Board of Review examined whether section 33 had been correctly invoked against an ophthalmologist who channelled earnings through a company. The Comptroller disregarded the corporate entity and treated amounts that had been paid as salary and one-tier exempt dividends as the taxpayer's employment income directly. The case raises important questions about when a corporate vehicle used by a professional will be looked through entirely.
What practitioners should take from this
The 124 invocations over five years, concentrated in dividend extraction and loan arrangements, signal sustained rather than sporadic enforcement. Both June 2026 judgments sit within that pattern: structures used by professionals, particularly in medical practice, to convert trading receipts into lower-taxed or exempt returns are receiving close scrutiny.
Taxpayers and advisers should review existing arrangements and ensure that a genuine, contemporaneous commercial rationale is documented. IRAS's track record suggests that arrangements which lack such justification, or where the documentation was assembled after the fact, will continue to attract challenge.