E-commerce has immensely benefitted Indian business communities, but at the same time, it has badly agitated Indian tax authorities and others worldwide. Indian tax laws (just like tax laws of any other nation) were drafted on the bedrock of “Classical Source & Nexus rule” and thus with the advent of the digital manner of doing business, Indian tax law as a whole appeared to be redundant. In this utter confusion, much to taxpayers’ annoyance, the Central Board of Direct Taxes started to tax the same income which was already taxed or proposed to be taxed by another jurisdiction. Against this background, the article attempts to navigate the journey that the Indian direct tax regime has made since the arrival of the digital economy taking along the way some hard experiences accosted and developments made based on the OECD’s BEPS Action Plans.