The OECD has made relevant progress towards reaching a consensus-based long-term solution to address the tax challenges arising from the digitalization of the economy and Pillar One is the last milestone of this tortuous path. In this article, the authors, without pretending to be exhaustive given the multitude of topics, wish to raise awareness among the international business community, illustrating some selected aspects deriving from Pillar One implementation that deserve further and deeper consideration in order to avoid triggering discontinuity to the current principles applied by MNEs to allocate income.