In this study, we examined how technology impacts adolescents' perceptions of, and affective responses to solitude, as well as how adolescents' own motivations for solitude (shyness, affinity for aloneness) were related to these reactions. Participants were N = 437 adolescents (297 girls; M[subscript age] = 16.15 years, standard deviation (SD) = 0.50) who were presented with a series of hypothetical vignettes asking them to imagine themselves in the context of pure solitude (alone in their room with the door closed), as well as being physically alone but engaged in increasing levels of virtual social engagement, including passive (e.g., watching videos, scrolling, but no direct social engagement), active (e.g., texting), and audio-visual (e.g., Facetime) technology use. Following each vignette, participants reported their perceptions of being alone and positive/negative affective responses. We also measured general motivations for solitude (shyness, affinity for aloneness). Among the results, adolescents perceived themselves as less alone in vignettes depicting increasing virtual social engagement. Affective benefits of increased virtual engagement were also found (e.g., less loneliness/boredom/sadness, greater social connection/contentment). However, these effects were moderated by solitude motivations, with different patterns evident as a function of participant shyness and affinity for aloneness. Findings highlight the importance of considering the nature of adolescents' technology use when alone, as well as motivations for solitude, when considering links between solitude and well-being.