In this article, the authors raise questions regarding the applicability of the recent OECD Guidance on Financial Transactions to the requalification of debt instruments as equity. The authors demonstrate that the current guidance is potentially inapplicable in many EU Member States and, perhaps, even in most OECD jurisdictions. Moreover, even where applied, such requalification might result in mismatches. Although Italy is taken as the example, the question addressed potentially involves a number of jurisdictions.