The jurisprudence governing workplace sexual harassment in India has undergone significant constitutional transformation since the enactment of the Sexual Harassment of Women at Workplace (Prevention, Prohibition and Redressal) Act, 2013. Although the Act codified the principles laid down in Vishaka v. State of Rajasthan, evolving employment relationships have required courts to reinterpret its foundational concepts in light of changing workplace realities. The Sexual Harassment of Women at Workplace (Prevention, Prohibition and Redressal) Act, 2013 (POSH Act) represents one of India's most significant legislative initiatives towards securing gender equality, workplace dignity, and constitutional protection against sexual harassment. While the enactment of the Act codified the principles laid down by the Supreme Court in Vishaka v. State of Rajasthan, the transformation of employment relationships over the past decade has exposed interpretative challenges concerning two of its most fundamental expressions, namely "aggrieved woman" under Section 2(a) and "workplace" under Section 2(o). The expansion of hybrid work arrangements, digital workplaces, contractual employment, consultancy engagements, educational institutions, and cross-organisational interactions has required courts to reconcile statutory language with changing workplace realities. This paper undertakes a doctrinal analysis of the judicial evolution of these concepts through an examination of landmark decisions delivered by the Supreme Court of India and various High Courts between 2013 and 2026. Drawing upon constitutional principles, statutory interpretation, judicial precedents, government reports, and contemporary legal scholarship, the study argues that Indian courts have progressively adopted a purposive and constitutionally informed approach that has significantly broadened the protective scope of the POSH Act. It identifies three distinct phases in this evolution, namely statutory interpretation, purposive expansion, and constitutional consolidation, demonstrating how judicial reasoning has ensured that the legislation remains responsive to evolving patterns of employment and workplace governance. The paper contributes to existing scholarship by proposing a three-phase jurisprudential framework for understanding the constitutional evolution of POSH jurisprudence during its first decade. The paper further analyses emerging debates relating to virtual workplaces, inter-organisational jurisdiction, procedural fairness, and institutional accountability. It concludes that while judicial innovation has substantially strengthened the Act's implementation, sustained effectiveness requires legislative refinement, institutional capacity-building, and greater integration of constitutional values into workplace governance. The study contributes to the growing discourse on employment law by presenting a coherent analytical framework for understanding the first decade of POSH jurisprudence in India.