Two trends – an ageing population and increasing income inequality – complicate the task of meeting the needs of those approaching or in retirement. Crafting effective regulatory responses, however, requires considering the causes of unequal outcomes in later life, especially the gender and other dimensions of the problem. Women workers suffer multiple disadvantages during their working lives, which result in significantly poorer outcomes in old age in comparison to men. This book sets forth our model of lifetime disadvantage, which captures the way in which gender and other factors play out in the lives of girls and women. Law and policy in the United Kingdom and United States fail to neutralise this complex, cumulative, temporally amplified gender disadvantage. We hypothesise that solutions are hampered by regulatory efforts that are disjointed and incremental. Real retirement equality requires that the vulnerability-producing conditions confronting women workers be tackled in a comprehensive and context-sensitive manner. Legal and policy paradigms geared to women’s life course are necessary.