Research has suggested that different strategies used when solving fraction problems are highly correlated with students' problem-solving accuracy. This study (a) utilized latent profile modeling to classify students into three different strategic developmental levels in solving fraction comparison problems and (b) accordingly provided differentiated strategic training for students starting from two different strategic developmental levels. In Study 1 we assessed 49 middle school students' performance on fraction comparison problems and categorized students into three clusters of strategic developmental clusters: a cross-multiplication cluster with the highest accuracy, a representation strategy cluster with medium accuracy, and a whole-number strategy cluster with the lowest accuracy. Based on the strategic developmental levels identified in Study 1, in Study 2 we selected three students from the whole-number strategy cluster and another three students from the representation strategy cluster and implemented a differentiated strategic training intervention within a multiple-baseline design. Results showed that both groups of students transitioned from less advanced to more advanced strategies and improved their problem-solving accuracy during the posttest, the maintenance test, and the generalization test.