The aim of this study was to develop and evaluate a learning strategy using critical thinking to teach dental students how to assess the risk of rapid oral health deterioration (ROHD) among elderly patients. A learning guide was developed using risk factors identified in the literature and the steps that expert faculty members apply in their clinical decision making, summarized in a set of ten steps. A new system of labeling risk was developed for the elderly population, which correlates the level of risk with the amount of disease. Participants in the study were all 91 fourth-year dental students in two subsequent classes who took part in a five-week Geriatrics and Special Needs Clinic rotation in the spring of 2015 and 2016. The students were introduced to the ROHD concept and asked to use the guide in a presentation during their rotation. The students were graded on an A, G, or M scale (Applied concept, Grasped and applied concept, or Missed application of concept). Students were also asked to assess their learning experience, and their answers were thematically grouped and analyzed. For eight of the ten steps, at least 93% of the students were graded A or G. The exceptions were the steps about developing a communications plan, which was missed by 23.1%, and self-assessment, which was missed by 30.8%. Interexaminer agreement on students' applying (A + G grades) versus missing the step was moderate or high on six of ten items. Nearly all the students (98.7%) considered assessing the risk of ROHD an important or very important skill. In this study, a learning strategy to teach dental students how to assess the risk of ROHD among elderly patients was developed and successfully implemented.