Some problems exist at the intersection of statistics and probability, creating a dilemma in relation to the best approach to assist student understanding. Such is the case with problems presented in two-way tables representing conditional information. The difficulty can be confounded if the context within which the problem is set is one where students have preconceived opinions on the direction of the potential association present. This article considers school students' responses to two problems of association, with data presented in 2 × 2 tables. A hierarchical rubric is presented to document students' understandings. Teachers' pedagogical content knowledge is also considered in relation to the same two problems. Findings include a surprising relationship of outcomes for students across the problem contexts and some concern about teachers' pedagogical content knowledge in this area of the curriculum.