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The idea that it is beneficial to place mathematics instruction within contexts that are relevant to students’ experiences is widely accepted in the culture of schooling. Here, we critically examine the principle of context personalization, or the idea that instruction personalized to student interests will enhance learning. We present the results of a randomized control study of 145 Algebra I students solving story problems on linear functions. We found that students in the personalization condition not only performed better while the treatment was in place, they were able to transfer this learning to future tasks. Context personalization acted as a form of perceptual grounding for struggling students, allowing abstract concepts in algebra to be more readily understood.