In Taiwan, the system of social work in the public school sector originated from the pilot project of the Ministry of Education in 1997. Initially, this involved providing professional counselors at junior high schools. Subsequently, the following localities also allocated funds to launch systems for school social work: Taichung County; Taipei City; Taipei County and Hsinchu City. A long-term stable development of the system requires comprehensive organizational planning, administration support, integration of related professions, and high-quality services provided by social work specialists. However, in the past five years, cities and counties have encountered several crises such as high turnover rates for social work professionals because of work-related stress, a deficient support system, and role ambiguity, etc. Therefore, the study investigated several sources of stress which could be affecting social work specialists in the public schools, including (1) the difficulties school social work specialists face in a school which does not value social work; (2) role conflicts between teaching and social work; (3) job insecurity because of fluctuating decision-making within the system; and (4) role ambiguity from different directions, such as the school bureaucracy, professional interests, government bureaucracy, and demands from clients. Through literature review and the author’s personal experiences, this paper proposed suggestions to resolve those issues.