Prior research has shown negative relations between math anxiety and math performance. We posit that one potential pathway through which math anxiety influences performance of math equivalencies is through help seeking behavior during learning. Here, we examine whether middle school students' behavior, specifically the frequency of hint requests, within educational technologies mediates the association between math anxiety and performance of math equivalence. Students completed a pretest measuring their performance of math equivalence and math anxiety prior to the intervention, and a posttest measuring their performance of math equivalence. We examine mediation in two online math learning technologies: From Here to There (FH2T) and ASSISTments. In both FH2T and ASSISTments, students can request hints that provide just-in-time support during problem solving. We examined whether the frequency of hint requests mediates the effects of math anxiety on performance in both conditions. Using multi-group mediation analyses, we found that math anxiety was not a predictor of hint usage in either condition when controlling for pretest performance. Further, we found that students with lower performance at the pretest used more hints in the problem set condition, and using more hints was associated with lower performance of math equivalence at the posttest. This relation was not significant in the FH2T condition, suggesting a fundamental difference in hint usage between the two technologies. These findings have implications for designing educational technologies that simultaneously promote math performance and productive help seeking behaviors in middle school students. [This is the online version of an article published in "Instructional Science."]