Despite a plethora of programs and policy interventions over the last forty years, limited progression has occurred for women into top leadership positions in organizations. It is the same in different sectors, different industries, and different countries. This chapter adopts a fresh perspective on this topic by focusing on the accumulated experiences of female employees’ life-cycle and women’s psychological attachment to their careers and employers. It reviews the distinct micro-aggressions experienced by subordinate women employees, coupled with the divergence of rhetoric and reality that accompanies their “equality of access” towards the top of organizations. Using a trust dynamics lens, the authors show how the impact of psychological contract breaches and violations is different for women, and can be responsible for transforming trust to distrust, diminishing their retention in organizational talent pools for elite roles. The chapter shows how the gender differences in HR policy outcomes from recruitment and selection, reward and recognition, and career progression can violate the psychological contract to induce sensebreaking negative anchoring events that undermine individuals’ psychological attachment to their careers.