For centuries, humanity gazed into icons and saw eternity. Now we gaze into screens and see only ourselves. The Eclipse of Freedom traces the long arc from the written icon to the digital algorithm, exposing how every invention - from printing press to smartphone - promised freedom but often delivered chains. Drawing on the insights of Plato, the warnings of Neil Postman, and the wisdom of the Orthodox Fathers, this book uncovers how technology fragments memory, weakens free will, and lures the imagination into shadows. From Gutenberg's press to artificial intelligence, the story is one of dazzling triumphs and hidden tyrannies. At stake is nothing less than the soul. For when man mistakes the machine for his mirror, he risks losing the image of God within.