For the last two decades, scholars have debated whether online activism has any effect in real life. Similarly, questions are always raised about how activist art or design does not affect real change and is even harmful in its fake pretentiousness. These debates are not new, as the argument had been made in favor of “street” activism as more courageous and change-enacting (compared to “armchair Marxists,” for example) long before the Internet was invented. In my talk, I shift these debates and discussions toward the question of freedom: what is freedom, for whom, and how to be free. My case study will be the Russian founded platform Telegram and how Belarus activists, especially artists, designers, and IT professionals, came together to appropriate Telegram in fighting for their freedom, and how the Russian and Belarus government officials and their allies have responded to maintain their power to decide who remains free and who is not. Finally, I will contemplate the role of a university library and an American academic institution as digital infrastructure, and faculty members, librarians and students as global digital citizens.