This paper addresses the potential conflict between freedom of expression and copyright law, pointing out how this conflict is developed in the context of new digital technologies. The study indicates that while new digital technologies and the Internet dramatically expanded the possibilities of each individual to access information and to express freely – often reworking content protected by copyright – the standards of copyright protection are increasing, both within domestically and internationally. In between these two gears (technology and copyright) that move in opposite directions, we find the constitutional guarantee of freedom of expression, whose relationship with the copyright has been largely ignored in Brazil and to a lesser extent, abroad. The paper presents an analysis of how these two rights of constitutional status dialogue, dispelling the notion no conflict could exist considering that existence of free expression safeguards built into copyright law. Departing from the dynamics imposed by new technologies, the study indicates that the right to freedom of expression needs to be reinterpreted and reshaped, pointing out some new frontiers where this emerging debate will take place.