By focusing on a particular alteration of the comparative likelihood task, this study contributes to research on teachers’ understanding of probability. Our novel task presented prospective teachers with multinomial, contextualized sequences and asked them to identify which was least likely. Results demonstrate that determinants of representativeness (featured in research on binomial, platonic sequences) are present in the current situation as well. In identifying a variety of context-related features influencing teachers’ choices, we suggest the context in which tasks are presented significantly influences probabilistic judgments; however, contextual consideration also provides researchers with potential difficulties for analyzing results. In addition, we identify strands for further research of contextual influence.