Despite their centrality to undergraduate teaching in U.S. universities, few studies focus on ITA's and their experiences within ITA training classes. Through a multiple case study of two In-Service ITA's (China, Taiwan) investments (Darvin & Norton, 2015) in one such class, it became clear how idiosyncratic are perception of these courses: one ITA's profound negativity involved accusations of institutional racism, yet another flourished through the class. Data included journaling, interviews/ stimulated recalls, course assignments, and classrooms (ESL and departmental) observations. Findings, presented as narrative then as conceptual configurations of investments, explained their experiences bifurcated due to their disparate teaching experiences and to policies decisions made within one's home departments. This study expands the scope of ITA and investment research by connecting macro and micro-level aspects. Pedagogical implications are to center pedagogy on learners' investments, utilizing reflexive activities to prevent misaligning the course with learners' identities, ideologies and desired capital.