Prior research on the affect heuristic demonstrated that the more a person likes an object or activity, the safer and more valuable it is judged to be. That relation was found when judging stimuli at the categorical level (e.g., nuclear power, airplane travel, heart surgery). Yet risk judgments and decisions usually pertain to specific instances of an object or activity rather than their categorical representations. We examined whether the relation between liking and perceived safety holds across multiple judgments of specific instances of an activity distinguished by contextual information. In four studies (N = 372), participants with domain-specific experience (backcountry skiers) completed multicue risk judgments under high uncertainty (judging the avalanche risk in backcountry skiing scenarios) and reported their degree of liking the scenarios. We demonstrate that the positive relation between liking and perceived safety holds across multiple judgments of specific instances of the activity. Furthermore, the liking-perceived safety relation (i.e., judging liked slopes to be safe, judging disliked slopes to be unsafe) held among backcountry skiers who like the activity and consider it safe at the categorical level. We discuss these findings from the perspective that contextual valence and perceived risk can dynamically diverge from categorical valence and perceived risk when perceiving specific instances of that category. These findings have implications for research on attitudes toward risk in extreme sports and other high-risk activities. Although it has been proposed that participants in extreme sports like risk and the thrill it provides, we found that backcountry skiers exhibit a healthy positive relation between liking and perceived safety when judging specific instances of skiing in avalanche terrain.