Postsecondary institutions are witnessing an increase in the number and severity of student mental health problems, necessitating an understanding of the difficulties these students encounter in striving for higher education. The authors conducted a critical interpretive synthesis of 10 articles pertaining to difficulties experienced by students with mental health problems and found that three synthetic constructs captured the nature of these difficulties: internal difficulties (physical, psychological, and social), external difficulties (structural and stigma) and academic outcomes (difficulties with disclosure and academic impairment). Findings are discussed in light of a critical exploration of the construction of problematics and assumptions in the literature. (Contains 1 table and 1 figure.)