The study of loneliness in the workplace has received extensive attention recently. However, there is a lack of research concerning loneliness within educational organizations and no study to date has examined loneliness among deputy principals. The current study examined deputy principals' interpretation of loneliness in the workplace and posed two questions: (1) How do deputy principals interpret their experience of loneliness at work, specifically in regard to how it manifests across different contexts? (2) What do deputy principals note as the reasons for their feelings of loneliness at work across different contexts? Based on 19 semi-structured interviews with Israeli school deputy principals, four distinctive themes of loneliness expressions were found: (1) loneliness perceived as separateness; (2) loneliness perceived as abandonment; (3) aloneness in carrying the burden of responsibility; and (4) aloneness in commitment to the school. From an analysis of the deputy principals' accounts, several insights are provided and practical implications are suggested.