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This community-based study examines the engagement of Afghan and Iranian newcomer parents in their children’s learning within Ontario’s middle school context. Grounded in an equity-based framework, it employed Cultural-Historical Activity Theory (CHAT) to identify contradictions between families’ culturally rooted expectations and their experiences navigating the Ontario schools. To address these tensions, I applied principles from Developmental Work Research (DWR) to co-design a Persian Parent Guide Booklet with participants and host community workshops, investigating the affordances of culturally and linguistically responsive tools. I used a descriptive phenomenological approach to collect parents’ lived experiences through semi-structured interviews, focus group discussions, and surveys with 12 immigrant parents, 6 Afghan and 6 Iranian. Findings revealed that while participants valued the inclusive and student-centered educational approach in Ontario, they expressed concern over a perceived lack of academic structure, discipline, and rigour. Moreover, they reported feelings of marginalization, citing communication barriers, the lack of familiar educational tools, and limited responsiveness to cultural and linguistic diversity. These tensions were further compounded by the perceived lack of peer networks, counselling, and institutional support to address settlement challenges. In response to the proposed mediating tools, participants reported that the Persian parent guide and workshops improved their understanding of school expectations, increased their confidence, and supported heritage language maintenance. Overall, by examining the perspectives of both Afghan and Iranian parents, this study offers a nuanced analysis of how culturally and religiously specific frameworks shape parental expectations and school engagement, underscoring the importance of culturally sustaining, linguistically accessible, and community-based approaches to parental engagement.