Schools are among the most important settings for the early identification of adolescents’ problems and support needs. However, the presence of counselors, screening programs, or referral mechanisms does not necessarily ensure that students gain access to effective support. This study aimed to identify barriers to help-seeking and to examine the role of schools in facilitating or hindering students’ pathways to receiving support. Using a qualitative approach and thematic analysis, the study involved 45 students aged 15–18 years in Mashhad, Iran. Participants were selected purposively, and data were collected through in-depth semi-structured interviews and analyzed using MAXQDA software. The findings identified the central issue as the “school’s failure to create a sense of safety and to effectively connect students with sources of support.” Students’ experiences were organized into three main themes: feelings of insecurity and punitive or disrespectful treatment at school; weaknesses in problem identification, counseling, and follow-up; and insufficient coordination among schools, families, and support services. The findings also showed that the way schools responded after a problem was disclosed shaped students’ subsequent help-seeking pathways. Respectful and non-judgmental responses, protection of confidentiality, appropriate referral, and continuous follow-up strengthened trust and access to support. In contrast, humiliation, breaches of confidentiality, referral without follow-up, and lack of cooperation from families or specialized services disrupted the support process and discouraged further help-seeking. The findings suggest that adolescent help-seeking is not merely an individual decision, but is closely shaped by the quality of relationships and the functioning of schools and other support institutions. Effective support therefore requires students to have access to services that are safe, respectful, responsive to their needs, and continuous.