This study identified the ‘service gap’ in high school counseling and examined factors that influence intention to seek help from Wee class school counselors. The analyzed factors were individual, namely psychological distress, counseling usefulness expectations, and self-concealment, and environmental, namely student-teacher attachment, social stigma, and Wee class setting. A total of 891 students at 3 high schools in Seoul responded to a psychological distress scale to identify the types of major difficulties they faced. Their intentions to seek help for reported psychological difficulties were also identified, and the results provided empirical evidence regarding gaps in high school counseling services. In addition, individual-environmental factors and intention to seek help from Wee class school counselors significantly varied by counseling experience and gender. These results indicate that a new operation and promotion strategy is needed for the Wee class of the current high school. Psychological distress had the greatest effect on the intention to seek school counseling followed in order of decreasing influence by social stigma and counseling usefulness expectations. Subsequently, student-teacher attachment and Wee class setting had the same effects. Based on the main research results, implications for enhancing high school students’ intention to seek help from Wee class school counselors and revitalizing school counseling were discussed.