The advancement of technology has significantly altered the characteristics of remote work in general, and cross-border remote work in particular presenting complex regulatory challenges. These challenges, with their linkage to a large set of work arrangements and locations, involve among other matters coordinating the relationship between labor law and social security legislation. An increasing number of remote workers are now able to provide services across borders, to markets and countries where they or their employers have no physical connection. As there are more employment regulations to choose from, this increases the possibility for the employer to exploit lower labor standards in other countries and avoid responsibilities towards their workers. Analysis of the literature and jurisprudence in different cases shows that new interpretations of the place of work are brought forward with the view to better protect cross-border remote workers, both in Private International Law and in Labor Law, considering the increasingly virtual nature of the workplace. However, the principle of territoriality remains a strong argument in the hands of higher courts to limit evolution in that direction.