This study examines the continuum of sustainability and corporate social responsibility (CSR) policies, and analyzes broad patterns that have emerged with respect to monitoring and evaluation practices in the CSR programs of Indian companies under new CSR regulations. Under these regulations, the Indian firms are mandated to spend at least 2% of their profits on social and development sectors. We specifically analyze (i) how Indian companies have conceptualized the idea of sustainability in their annual sustainability reports, and how these ideas get reflected in their CSR policies, and (ii) the monitoring and evaluation practices in CSR interventions. The study uses both primary and secondary data sources, and employs text network analysis and narratives-based content analysis to analyze the data. We find that the conceptualization of sustainability is a largely rhetoric and customary exercise that does not take into account variations in firms’ businesses. This approach toward sustainability initiatives presents serious challenges to sustainability, including social sustainability. The study also finds that there is lack of ‘willingness’ and ‘readiness’ among Indian companies to measure and monitor the outcomes of CSR interventions, which is arguably one of the most robust ways to signal their commitment toward corporate sustainability. Although mandatory CSR spending is a recent phenomenon in India, our study establishes that it is only through the design of effective CSR policies that the best practices for Indian business community can emerge in the near future.