Historically, offences considered “impossible” of commission have been problematic for the law of attempts. In particular, there is no consensus as to whether there is a legally relevant difference between the concepts of “factual impossibility” and “legal impossibility.” This is significant not only because it possesses implications for legal and moral responsibility, but also because it highlights uncertainty in the law. The current study examines how impossibility affects judicial decision-making in criminal attempt cases. A qualitative content analysis was conducted on case law from three Commonwealth countries: Canada, New Zealand, and Australia. The results indicate that inconsistency in the approach adopted towards impossibility attempts is a consequence of differing doctrinal frameworks. Because Canada and Australia generally adopt the subjective approach (in contrast to New Zealand, which generally adopts the objective approach), it is not surprising that they rely on consequentialist rather than retributivist rationales of punishment. Furthermore, despite being criticized as an area of law based on “abstract conceptions,” this study demonstrates that impossibility cases raise broader social policy issues.