The case study is about a group of companies engaged in education, steel fabrication and oil businesses owned by a single proprietor. The company was based in Fatehnagar which was part of Hyderabad district in the state of Telangana, India, and the case study traces the origins of the group from 1960s to 2021. The group was invested the surplus cash flows from the oil business to initiate and expand other businesses during this period. The economic downturn due to the COVID-19 pandemic had hit the company, particularly its oldest business – Noble Chemical Agency. The oil business was facing issues related to its growth and profitability, and the uncertainty around COVID-19-related restrictions had only augmented the fears of the management. The case study looks at issues and the dilemma which the owner of the company faced. The case study highlights various issues related to working capital management, especially related to receivables management and inventory levels faced by businesses during the slow-growth phase. It demonstrates how working capital management issues, if not resolved in time, can lead to insolvency of even a successful company with a sound business model.