Liability insurance concerns an insured’s insurance of its legal liability towards a third party for the latter’s loss. This specialised type of insurance is rather neglected in South African insurance law. There is a lack of understanding of the intricacies of liability insurance and its unique challenges. This flows primarily from its complex nature as third-party insurance, which involves legal obligations between multiple parties, and a lack of statutory regulation of the distinctive contractual aspects of liability insurance. Furthermore, limited authority exists on contentious legal aspects as a result of the relatively small number of judicial decisions in this field of law. It is also evident that liability insurance constantly evolves as new grounds of liability emerge and new insurance products develop in response to the changing demands of society. The rise of consumerism and the increase in third-party claims amplify the economic significance of the law of liability insurance in South Africa. A substantial knowledge gap remains in our jurisprudence, irrespective of the recent introduction of new statutory instruments aimed at regulating insurance practice in general. These reforms have not as yet been applied critically to liability insurance, and no specialised legislation in South Africa regulates aspects of this branch of insurance as is the case with microinsurance. The focus in this thesis is on two main issues: the insurer’s duty effectively to indemnify the insured, and the insurer’s defence and settlement of third-party claims brought against the insured. As a subsidiary theme, this thesis analyses legal uncertainties that may persist during pre-contractual negotiations, the liability insurance contract lifecycle, and even after the expiry of the contract. Legal challenges can be addressed by novel and creative application of the national law. Potential solutions can be gleaned from the other progressive jurisdictions reviewed – English and Belgian law. It is evident that this research may prompt Parliament to develop specific rules and regulations for liability insurance contract law. This thesis includes a check list of some of the most important disclosure duties for procuring liability insurance cover, its operation, and claims processes. / Mercantile Law / LL.D.