Gender discrimination in academia is well documented across different countries and academic systems. Moreover, the phenomenon is especially persistent, given that we are in front of more than 20 years of gender equality interventions, across Europe and the USA. This chapter starts by providing a brief overview of the main theoretical perspectives and issues debated in international literature on the topic. Then, it focuses on Italy and develops along four topics. First, the features of the Italian academic system are discussed. Second, it presents the most common approaches and measures to tackle gender inequality. Then it focuses on two key moments for an academic career: the very first steps, and subsequently the progression to top (full professor) positions. Overall, it shows that, despite some important advancements and pockets of good practice, the progression towards equality is very slow, with some issues at entry level which deserve careful monitoring.