This paper deals with the doctrine of substance over form in so far as it relates to committing fraud on the law (or the doctrine of fraus legis), and the connected question of when a transaction can be said to be simulated. These three doctrinal concepts are inter-linked and their interstices will be explored with reference to the case law. The aim is to shed light particularly on the last issue – simulated transactions – and to answer the question whether dishonesty remains a requirement for a finding that a transaction is simulated. This enquiry is prompted by dicta in the recent case of NWK which tend to suggest that in certain circumstances a transaction might be deemed to be simulated even in the absence of fraud.