In the so-called “digital age,” postal services are yet again being challenged. While they had already faced a significant challenge during the “age of liberalization,” the present challenge appears to be more serious, particularly in terms of its effect on the letter segment of the postal services. The aim of this introductory chapter is to place the challenge of the digital age within a broader historical, commercial, and political context of postal operators. Indeed, while postal operators have been quite successful at mastering the challenge of liberalization, the question now is whether they will also be able to master the challenge of the digital age, which I believe is a more fundamental challenge. I will try to address this question by way of a more historical approach. The history of postal operators and the postal sector more generally can be broadly structured into three phases: the phase of “quiet life” before liberalization (that is, before the 1980s), the phase of liberalization (roughly between 1990 and 2005), and the digital age (starting around 2005). These three phases also constitute the structure of this chapter, although the chapter's main focus is on the recent challenge of the digital age. I will conclude with some considerations about the future of the postal sector in general and, in particular, the future of historical postal operators beyond the digital age.