This article outlines the main concerns and drawbacks that one could confront in attempting to analyse financial transactions by following the principles provided in the Transfer Pricing Guidance on Financial Transactions published by the OECD on 11 February 2020. In essence, it highlights the necessity of assessing the company’s creditworthiness and the applicability of the various tools and methodologies available for the identification of the appropriate credit rating of MNE groups and subsidiaries, as well as the validity of the contiguous interrelations between the assets and credit rating of the guarantor with those of the borrower. At the same time, this article specifically aims to provide a practical illustration of the rating methodologies developed by credit rating agencies and thus make it a self-explanatory example for use in the endless discussions regarding the importance of qualitative reasoning for the estimation of the borrower’s credit rating.