The article deals with the recent case law of the Italian Supreme Court in respect of the application of the Parent-Subsidiary Directive. In the timeframe between 2017 and 2019 the Supreme Court issued four judgments which denied the application of the dividend withholding tax exemption regime based on a restrictive and highly disputable interpretation of the ‘subject to tax’ requirement laid down under Article 2(a) (iii) of the Parent-Subsidiary Directive. The article analyses this interpretative approach and highlights the reasons of its non compliance with the principles underlying the Parent-Subsidiary Directive. Then the article analyses a further and more recent judgment of the Italian Supreme Court in which the Court seems to change its approach, clarifying that the dividend withholding tax exemption regime applies even in cases in which the parent company is merely liable to tax in its State of residence, being not required that the dividends received by the parent company are subject to tax in that State. In the conclusions the author expresses his view on possible amendments to the Parent-Subsidiary Directive which could contribute to a more straightforward application of the regimes provided by the Directive in the different EU Member States.