Adolescence is characterized by heightened sensitivity to social belonging, making loneliness prevalent and consequential for youth. Maladaptive personality traits may further exacerbate loneliness. In this preregistered 14-day Ecological Momentary Assessment study, we examined loneliness across social contexts and timescales in relation to maladaptive personality traits among N = 294 adolescents aged 12–21 years (Mage = 17.5, SD = 2.64; 58.5% female; 86.73% born in Germany). Participants answered 27,503 of 32,340 momentary prompts, indicating high compliance (85.1%). Loneliness (βmomentary = 0.51; βdaily = 0.67) was higher when participants were alone, yet only the presence of close others (e.g., friends) – not weaker ties (e.g., classmates) – reduced loneliness (β = –0.39 to –0.62). Youth who were alone more frequently did not report higher overall loneliness. Maladaptive personality traits were associated with higher (βmomentary = 0.32; βend-of-day = 0.40) and more variable (βmomentary = 0.31; βend-of-day = 0.34) loneliness but amplified the effect of being alone on loneliness only on the between-person level (β = –1.13). Exploratory analyses indicated that social satisfaction partially mediated the association (β = 0.50). These findings underscore the importance of both structural and qualitative aspects of social environments, as well as personality-related vulnerabilities, to better understand loneliness dynamics in youth.