This article explores the intricacies of capital maintenance under UK Company Law, tracing its historical roots, pivotal principles, and the legislative safeguards devised to uphold creditor interests. Originating as a judicial response to the inception of limited liability, the doctrine has matured into a robust regulatory framework central to company operations. Fundamental to this evolution are landmark cases such as Flitcroft's, which have anchored the principles ensuring corporate solvency and creditor protection. Nevertheless, the dynamic financial landscape presents its own challenges. The downfall of Polly Peck International in the early 1990s stands as a stark testament to the dangers of neglecting these principles, spotlighting the severe repercussions of financial misdemeanours and unchecked expansion. Additionally, with innovative financial instruments, such as convertible bonds and financial derivatives, traditional boundaries between debt and equity are becoming increasingly indistinct. This evolution prompts a critical reassessment of whether existing capital maintenance rules are adequately equipped to navigate the complexities of today's corporate realm.