Over the past four decades, Indian Information Technology (IT) industry has been delivering traditional software and BPM (Business Process Management) services to its clients across the globe. Providing cost-optimized, yet high-quality services following standard process methodologies has made it an attractive destination to clients across industry verticals. Today, the challenge before this industry is to provide emerging technology solutions to clients in their digital transformation drive. Situated at this pivotal juncture in its journey, the ‘work from home’ (WFH) norm during to the recent COVID-19 pandemic posits challenges of a new kind for this sector. We explore these challenges based on our four-month ethnographic study (Jan-May, 2020) in a service-based IT organization situated in Bengaluru, which over the past five years has been developing Artificial Intelligence (AI) based solutions to its clients. © 2020, IFIP International Federation for Information Processing.