Over the past few years, remote working has become a remarkable trend in business operations. This paper delves into the complexities of cross-border remote working within multinational enterprises (MNEs) in the post-Covid era, examining the profound tax implications it presents. It scrutinizes the potential for remote working arrangements to create permanent establishments, influencing the jurisdictional rights to tax business profits. The research explores the nuances of the current international tax framework, highlighting areas of ambiguity and the need for a more harmonized approach to prevent double taxation. Furthermore, it discusses the intricacies of transfer pricing issues that arise from remote working, emphasizing the importance of aligning transfer pricing models with the arm’s length principle. Through a series of case studies, the paper offers practical insights into how the permanent establishment and transfer pricing framework applies in real-world scenarios, ultimately advocating for policy reforms and more explicit guidelines to address the emerging challenges of remote working in a globalized business environment.