Throughout the world, the role of working women has altered drastically due to social demands and economic circumstances. This has also contributed to working women undergoing immense pressure to develop a career as vigorous and holistic as their male counterparts while retaining active involvement in personal life as well. However, managing menstruation at the workplace is one of the most overlooked issues that call for immediate attention and support, as it hinders the performance and efficiency of women at the workplace. In India, menstruation is still considered to be something dirty or impure due to antiquated beliefs and traditions, and the word menstruation is met with raised eyebrows and repugnance. The initiative of menstruation leave policy would be a helping hand towards women who suffer from extremely painful and uncomfortable menstruation and need a day or two off to rest at home and return back to work with a fresh mind to contribute to the productivity of the organization. Menstruation Benefits Bill, 2017 has been tabled in the Parliament that seeks to provide working women in both private and public sectors paid menstrual leave of two days every month in addition to the sick leaves. However, not acknowledging the core stigma, gender discrimination, sexist beliefs, or menstruation leave could invite adverse impacts on women. It would not be easy to implement Menstruation Benefit Bill, but it is a much-needed shift in the right direction. The paper discusses the significance of menstrual leave and analyses the merits and demerits of implementing the Bill in India. The paper further reflects upon other initiatives that challenge menstruation stigma and subsequently concludes with suggestions.