The United Nations Model Tax Convention (UN MTC) much like the Organization for Economic Cooperation and Development Model Tax Convention (OECD MTC) deals with taxation of cross-border employment incomes. While the OECD MTC professedly promotes economic interests of advanced Global North states, the UN MTC intends to protect fiscal interests of developing countries lying in the Global South. Article 15, unlike most other provisions of the two MTCs, had a rather smooth sail until the turn of the century when digitalization began to very rapidly grip the world economy. In an effort to grasp the digitalization-induced disruption in the application of UN MTC Article 15, a romantic prototype of ‘digital nomad’ was contrived by Global North scholars to denote remote working of various shades with an ostensible intent to attempt the decadesold allocation of taxing rights between the source and residence states. This article posits that the concept of ‘digital nomad’ only pertains to the Global North, and it is completely alien to the developing countries. It further argues that the Global South’s competing challenge is the ‘digital freelancer’ that has not yet been allowed to realize its full potential due to countermeasures introduced in Global North states. Unlike the digital nomad who moves freely across borders without any visa restrictions exercising services remotely for an employer(s) based in distant lands, a digital freelancer is permanently ‘caged’ inside his own (developing) country and renders services for his employer(s) located elsewhere in the world – majorly due to visa restrictions. It is premised that the digital nomad and digital freelancer being intrinsically distinct phenomena from each other pose varying challenges to the different tax administrations of the Global North and Global South. This contribution aspires to seminally conceptualize and sharpen that distinction and focus on the latter. The objective is to emphatically project the Global South’s perspective on Article 15s operability in a digitalized world and reset its international tax agenda for engaging with the Global North on more equitable terms.