As emotions research in the field of second language acquisition continues to evolve, it is equally important to explore the impact of social–emotional variables that are specifically relevant to heritage language (HL) contexts. Anchoring on foundations in critical heritage language education (HLE), this study examines the discomforts of the HL classroom from a diverse heritage speaker (HS) perspective. Additionally, comforts that support the HL classroom as a safe space for emotional security and well-being for HSs across HLs are explored. Examining the HL classroom from the perspective of HL practices and knowledge systems, this study ultimately aims to: (a) outline the emotional complexity of HL pedagogical spaces, and (b) provide concrete and meaningful recommendations for supporting HS well-being and HL development from a transformative positive psychology lens. Data for the current qualitative study were provided through two separate methodologies. First, 64 HSs of Spanish responded to a qualitative questionnaire probing the emotional reactions and memories instigated by authentic HL classroom reading material on sensitive topics of racism, bilingualism, and immigration. The themes identified in written narrative data through an inductive thematic approach were then used as a foundation for semistructured interviews with language learners (n = 6) and educators (n = 8) from eight different HL backgrounds. Findings revealed feelings of comfort and discomfort, and even trauma and healing, in HLE spaces rooted in (a) language learning experiences, (b) social memories of (dis)comfort, and (c) intergenerational histories. Together, the data suggest how the HL classroom can act both as a trigger of social injustice, linguistic insecurity, and family conflict and, at the same time, as a space instigating affective reactions associated with social rebellion, linguistic confidence, intergenerational healing, and emotional refuge. Specific pedagogical recommendations are made to equip educators with a concrete toolkit for the HL classroom.