In coastal defense operations, anti-ship missile (ASM) attacks on amphibious assault high value targets (HVT) constitutes a window of opportunity with decisive potential. However, in war, the availability and performance of ASM-forces is uncertain and most likely less than ideal. This thesis explores how organizational and technological flexibility can be a solution to such uncertainties. This is achieved by modeling representative examples of weapon redundancy, weapon versatility, and a flexible balance between offensive and defensive powers. A Two-Layer Defense HVT Acquisition Missile Salvo Model is developed, as an extension of Hughes Missile Salvo Model, to enable detailed study of sub-saturation attacks that rely on missiles leaking through target defenses. The result of this study shows that organizational and technological flexibility can potentially enhance ASM-attacks directed at the HVTs of an amphibious assault in multiple ways. Mentionable key-findings are that additional ways of challenging target defenses, additional firepower, and increased lethality through characteristics such as precision will create tolerance to loss and tactical benefits.