An increasing number of women are becoming empowered with changing cultural dynamics, gender equality, education and technology. The use of Internet and social media platforms by businesses at various stages is on the rise. Despite its benefits, women entrepreneurs in developing countries are less inclined towards using the online mediums for their business in comparison to men. This study observes activities where women entrepreneurs use online mediums for business purposes, understands challenges faced in doing so, reasons behind such challenges and how do they deal with them. Qualitative research is conducted via semi-structured interviews with women entrepreneurs at India. Findings indicate that there are commonly prevalent issues faced by Indian women entrepreneurs while using online mediums. As a way out, they either choose to shy away from digital mediums or seek external help. They are more comfortable using digital mediums where the communication and onus is one way, there is limited need to trust the other person or there is less possibility of receiving damaging comments in public. For interactive activities, women refrain from using online mediums. Financial, social and cultural factors also play a role in keeping women entrepreneurs behind from using online mediums for their business.