Flexible working refers to those working arrangements that are significantly different from regular work patterns. It allows employees to choose his/her place or time of work by exploiting the technological advancements that makes it possible to connect to work virtually without having to commute to office and/or do so during hours of the day that suits a particular employee. While men and women can be beneficiaries of such flexible working arrangements, it is the Woman Professional who is also more often expected to be responsible for child care, elder care and household duties and to whom the choice of working flexibly serves as a critical enabler and sustainer of her career. This cross industry study brings to light the barriers that mar the successful implementation of flexible working policies in Indian Corporate offices. It was found that the challenges to flexible working in could be broadly classified as 1) Cultural 2) Infrastructural and 3) Attitudinal. The findings of the study helped us conclude that the ingraining of flexible working in an organization’s work culture calls for concerted effort from the employers’, the women professionals’ and their families’ end.