This article is concerned with source-based approaches to the international tax challenges raised by the digitalization of the economy. It focuses, in particular, on what, in the current debate, is often referred to as a possible set of short-term or interim measures. After introducing the context from a broader socio-historical and business perspective, the article addresses the current complex tax policy agenda, aiming at outlining possible policy models to be derived from the OECD and EU “platforms for proposals”, as well as from selected domestic experiences. In doing so, the article addresses a set of micro-research questions that appeared very relevant to the author in the current climate of uncertainty surrounding the taxation and digitalization agenda. First, the article is concerned with the need to conduct an exposition of terms by introducing some clarifying distinctions against the backdrop of the very blurred lines between the various policy options under consideration. In particular, it attempts to shed light on how a short-term or interim approach could actually be defined and in tracing some boundaries between equalization levies and a withholding tax-based approach. This exercise allows for some possible proposals to be set forth regarding how the concerned measures may be made more easily compliant with the pre-existing international legal framework and more attuned with their inherent policy objectives, also bearing in mind the need to minimize distortions as far as possible. This normative perspective is inherently tied to another set of ‘micro-research questions’ addressing how the policy and legal planes interact in this area and to what extent such initiatives might be pursued in accordance with a coherent set of policy goals in a way that would not prove disruptive for the existing legal framework of reference. In attempting to do so, however, the author realizes that there may be a clear trade-off between the above different sets of concerns, so that the undertaking of any action would need to implicitly express a fundamental option in that regard. Such findings are substantiated against the backdrop of some key unilateral experiences (including regional ones, as per the recent Directive proposal on the common system of a digital service tax) that have so far been enacted or ventilated, assessed in particular in the light of the recently released Interim Report on the Tax Challenges Arising from Digitalization.