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“The internet dilemma” was the concept used to describe luxury brand companies' initial reluctance to integrate online technologies into their business model. However, over time, luxury brand companies have understood that moving towards digital transformation is the only way to survive on the market and appeal to the new luxury brand consumers. In a few years, digitalisation has become a priority for all luxury brand companies that started to integrate digital and physical platforms to engage consumers through all touchpoints of their shopping journey. In light of the topic's relevance and considering the primary focus of research on consumers, this chapter aims to deepen the digitalisation phenomenon in the luxury market involving the little-explored luxury brand managers' perspective. The authors conducted a longitudinal study to compare the main changes in integrating digital and physical platforms from the managers' perspective between 2014 and 2020. In this endeavour, they also considered how the COVID-19 pandemic had affected luxury brand companies' digitalisation.