Whereas teachers’ Stages of Concern (SoC) and their Technological, Pedagogical, and Content Knowledge (TPACK) appear to be related constructs, studies are scant regarding the connection between these two research areas. This study intensively examined the association between Taiwanese senior high school teachers’ SoC and TPACK through a national survey (N = 605) and canonical correlational analysis. To ensure rigor of study, we revised a TPACK instrument for Taiwanese senior high school teachers, statistically tested SoC’s developmental phases, and reworked the Stages of Concern Questionnaire. Three canonical correlations became evident, portraying a significant connection between SoC and TPACK and further supporting our hypothesis that a higher level of technology integration would correlate higher with more synthesized types of teacher knowledge. Recommendations were put forward regarding support strategies of change facilitators, as well as directions for future research.