Section 423 of the Insolvency Act 1986 allows courts to unwind transactions entered into to prejudice creditors without requiring proof of dishonesty or fraud. Recent case law has nevertheless treated such claims as inherently alleging “disreputable” conduct, with significant implications for privilege and pleading requirements. This article examines the iniquity exception to privilege in s 423 claims, with particular focus on the November 2024 decision in Invest Bank v El-Husseini [2024] EWHC 2976. That decision suggests that establishing a prima facie case of an undervalue transaction entered into for the statutory purpose engages stricter pleading rules and displaces privilege. However, uncertainty remains about the boundaries of this presumption of inherent iniquity and its practical implications for privilege loss across s 423 cases.