This paper draws upon existentialism, play theory, and game studies and makes use of first- person insights on Pocket Planes (2014) in order to address questions pertaining to the nature of freedom in single-player computer game play. On one hand, this paper could be read as a critique of Pocket Planes . On the other, it focuses on Pocket Planes as a case through which to examine the usefulness of the idea of ‘free play’ for the description of the interactions we have with single-player computer game artifacts. First, I shall briefly introduce Pocket Planes to give the reader a context, and then proceed to cross-expose concepts from Fromm’s dualistic notion of freedom with ideas of play from Hendricks and Fink. I shall then analyse how the experience of playing Pocket Planes matches with this constellation, and proceed to discuss what the analysis could possibly tell us about freedom and play on a more general level.