The persistent underrepresentation of women at senior and mid-career levels in the information systems (IS) sector—the “broken rung” problem—is extensively recognized. However, the understanding of its underlying causes and effective solutions is still lacking. Through collaboration with five multinational technology firms in Singapore, we recruit high-quality participants to explore the broken rung problem. Our findings reveal that microaggressions substantially diminish the psychological safety of mid-career women in the ICT field, reducing promotability perceptions and lower job satisfaction. Concurrently, allyship is identified as a potential mitigating factor, buffering the adverse effects of microaggressions by bolstering mid-career women’s psychological safety. Interestingly, our results indicate that men overlook these dynamics, which suggests that “privilege blindness” exists in the ICT field. This calls for further efforts to enhance organizational awareness and create actionable strategies such as cultivating allyship within organizations to solve the broken rung problem.