The contemporary genre of software art is characterized by creative and critical engagement with the technical language of computer programming. While at one level this represents a new realm of artistic possibility, at another level it raises fundamental questions concerning how aesthetic practices can intervene within processes of logical abstraction and instrumental engineering. This monograph argues that the potential of software art resides less in defining a settled and clearly delineated creative field than in opening up a space of vital aesthetic risk in which a variety of discursive boundaries can be challenged. It begins by examining the notion of software within computer science and new media theory, moves on to provide an overview of the emergence of software art, and then considers a range of specific dilemmas - of cultural position, of aesthetic visibility and of recursive focus - that the genre confronts. These dilemmas are addressed both generally and in relation to aspects of the author's own software art practice. This monograph should prove interesting to theorists and practitioners in the fields of media, new media and software art.