Educational constructivism has long been associated with advanced pedagogy on the basis that, it champions a learner-centered approach to teaching, advocates learning in meaningful contexts and promotes problem-based activities where learners construct their knowledge through interaction with their peers. Involving language learners in video projects allows a seamless incorporation of constructivist assumptions into the teaching and learning experience. However, practicing educational constructivism has been fraught with a number of pedagogical dilemmas and challenges (Windschitl, 2002). First among these dilemmas is the need to promote learner autonomy while, at the same time, maintaining a solid framework for the learning experience. Secondly, constructivist teaching and learning require proper assessment strategies that take into account the uniqueness of this educational practice. This article describes a video project implemented by Russian language learners and deliberates on possible ways to deal with these pedagogical dilemmas.