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The participants were 885 Finnish adolescents (mean age\u2009=\u200915.74, SD\u2009=\u20090.37, 56% girls). Loneliness was measured twice: in Grade 9 and at the beginning of upper secondary school in 10th grade. Psychological inflexibility and the closeness of friendships in school were measured in Grade 9. Results showed that a high level of psychological inflexibility in Grade 9 was associated with higher loneliness at the beginning of upper secondary education and increased loneliness during the educational transition. Furthermore, girls' (but not boys') friendship closeness in school partly mediated the association between psychological inflexibility and loneliness. The results suggested that psychological inflexibility is a social risk factor for loneliness among adolescents transitioning to upper secondary school. 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