Understanding reaction mechanisms is integral to success in organic chemistry; however, prior research suggests that learners struggle with recognizing the importance of underlying implicit features in reaction mechanisms. Because of this struggle, understanding how learners' reason about reaction mechanisms and developing assessments to elicit certain types of reasoning has been a topic of great interest in organic chemistry education research. Much of the work with assessments and learner reasoning focuses on scaffolding simple reaction mechanism prompts; however, what has not been focused on is how modifying the levels of prompt support impacts learner reasoning. This work seeks to evaluate the impact of varying cueing in constructed-response assessment prompts on the level of explanation sophistication for nucleophiles and electrophiles. Assessment prompts utilize five reaction mechanisms commonly taught in first-semester organic chemistry. Previously reported nucleophile and electrophile rubrics were used to analyze 2,079 written explanations by learners. Our data for all five reaction mechanisms suggest that our highest cued prompt somewhat elicits higher levels of explanation sophistication. However, when each reaction mechanism is considered individually, we found no differences between the prompt used and level of explanation sophistication for three of the five reaction mechanisms. Our data suggest a more inconclusive overall finding. We emphasize the instructional context, learners' knowledge limitations during assessment, and the extent to which more cueing and scaffolding in the assessment item is necessary to elicit desired responses. Our results confirm that assessments drive learning, even when considering a null and nuanced finding of our study.