The intelligent tutoring system of structure strategy (ITSS) is a web-based digital tutoring system proven to be effective in helping students recognize and use text structures to comprehend and recall texts. However, little is known about the dynamic learning processes within the ITSS. This study aims to investigate the effects of feedback dosage on lesson mastery throughout the progression of ITSS lessons. We applied a confirmatory factor analysis and extended vector autoregressive model to assess the dynamic relationships among three tasks embedded within the ITSS and found: (1) significant cross-regression effects among the three reading tasks; (2) distinct effects of feedback dosage on the specific reading task; and (3) different effect sizes of feedback across lessons. Results provide helpful insights on ways to design better modules in further development of the ITSS.