Matriculation to college life can often pose adjustment problems that require identification and help. This is especially true in societies where gender separation is the norm. This qualitative study explores the help-seeking process from the subjective and cultural perspective of Omani students. The processes of help-seeking behavior within the Omani cultural framework are explored in terms of recognizing, defining a problem, making decision, and selecting sources of help. A triangulation methodology was used in this study that included two and half months of observation and interaction at Sultan Qaboos University in the office of Deanship of Student Affairs, the Counseling Center, and the Psychiatric Department of the university hospital. Individual and focus-group interviews were conducted. The interviews were, for the most part, extensive dialogues. Statistical documents in regard to students’ academic probation as well as newspaper articles aided in understanding the Omani help-seeking process. The results show that Omani students experience multiple challenges that impact their psychological adjustments. These challenges can be associated with the novelty of academic life and the coeducational culture of the institution. Some freshmen face with new expectations of learning as well as separation from their close ties, and struggle to find a balance between some of their traditional points of reference and the new sets of values to which they are exposed at Sultan Qaboos University. The influence of traditional culture on the dynamics of problem recognition may be expressed by anger and rejection, declining academic achievement, and violation of religious principles. For these students, traditional values and religious practices are seen as key coping mechanisms.