In Indonesia, English is the first foreign language taught to students from the beginning to the university level. It is one of the educational programs that must be increased and developed at schools in Indonesia. In vocational high schools, students are prepared to speak English for communication when they work in companies. Unfortunately, speaking competence is difficult because effective oral communication requires some aspects of using the language appropriately. The most common psychological problems in speaking English faced by students in speaking English are (1) lack of confidence, (2) lack of motivation, (3) fear of mistakes, (4) shyness, and (5) anxiety. This study employs descriptive qualitative that aims to describe the psychological problems in speaking English faced by the tenth, eleventh, twelfth, and thirteenth-grade students at SMKN 1 Singosari Malang. Qualitative descriptive contains sampling, data collection, and data analysis. Therefore, the researcher used two instruments: a questionnaire and an interview. Based on the obtained data, the most psychological problems in speaking English faced by students were fear of mistakes and anxiety. However, the least one was a lack of motivation, which was not as serious as others. The problems were caused by environmental aspects such as being judged as well as being nervous if they spoke in front of other people and some factors such as self-motivation, hereditary factors, personality disorders, side effects of certain medicines/substances, and experience in using English successfully. Based on the interview result, in order to overcome the students’ problems, the students with high proficiency skills in speaking had some strategies, namely memorizing vocabulary, practicing more and more with friends, listening to Western music, watching films, making friends with native speakers, speaking in front of a mirror in order that they can see their style in speaking, joining English club or course, talking to themselves, making an English day in class, and conducting English games. Meanwhile, it is suggested that English teachers should pay more attention to students' psychological problems in speaking English, use a suitable method in speaking class, and train students to speak a lot in front of other people.