The aim of this article is to assess the Italian and Singapore regulatory framework in the area of transfer pricing with reference to a possible use of the blockchain technology. For this purpose, it conducts a comparative analysis, focused on two fundamental issues in national legislation: the burden of proof and the penalty system. Based on the results of the analysis process, the conclusion is that in both countries some changes in legislation should be considered to ensure legal certainty and properly motivate multinational enterprises and tax administrations towards a blockchain scenario for transfer pricing.