This study explored how 60 trilingual immigrant youth interpret and make sense of their educational experiences in Israeli schools. Conceptualizing the language knowledge of multilingual individuals as one unitary system, the study is based on the assumption that a fuller understanding of students' educational experiences can be obtained by examining their written expression about school experiences in the three languages at their disposal: Russian (L1), Hebrew (L2) and English (L3), which were elicited via letter writing tasks. A total of 180 letters (60 letters in each language) were analysed through qualitative content analyses revealing five interrelated themes depicting immigrant youths' scholastic studies as a complex multifaceted experience intertwined with issues of language, culture, identity, and social struggles. The findings provide insights into how the language repertoire of immigrant youth is powerfully linked to their sense of self, educational circumstances, and acculturation.