In their daily teaching in hospitals, teachers interact within a complex interpersonal and professional network. The present study investigated what kind of professional relationships hospital teachers have with other staff in their daily work and which factors they perceive as being either stressful or gratifying in their professional activities. An online questionnaire consisting of multiple-choice items and open-ended responses was developed and distributed to all school-in-hospital teachers in Italy. A representative sample of 602 teachers responded. Quantitative findings were analyzed using descriptive statistics. The open-ended responses were analyzed by combining qualitative content analysis with statistical textual analysis using T-LAB software. The results confirm the complexity of the setting in which hospital teachers operate, one that is characterized by the wide variety of professional and non-professional roles the teachers perform. Four clusters were defined covering both the stress dimensions (Illness, Work Fragmentation, Organization, and Interpersonal Relationships) and the gratifying aspects (Work Recognition, Normalization, Human Contact, and Interpersonal Relationships). The implications of these findings for the management of hospital schools are discussed.