One of the main factors contributing to students' optimal development in school settings is the implementation of appropriate differentiating and individualizing measures. While this topic is well researched and addressed in the context of primary and lower secondary education, the theoretical and empirical research on differentiated and individualized teaching in vocational education and training (VET) programs is relatively scarce. However, well-applied individualization measures seem equally important in the context of VET programs, as they are frequently attended by students with lower educational aspirations, diverse socio-cultural backgrounds, and complex educational and personal needs. Our research explores what kind of individualization practices exist in Slovenian VET programs and what roles teachers and school management play in implementing individualized teaching. A single case study with one class of 16-year-old students (N = 22) attending the confectioner VET program was conducted. The data were collected by means of interviews, observations, and questionnaires, and were analyzed and interpreted by combining qualitative and quantitative methodological approaches. The results indicate that the school strove to address the diversity of the student population and used a number of different activities at institutional (school) as well as individual (teacher) levels. However, the potential of a more individualized approach seems to be largely unexploited. It is necessary to understand individualization as a principle implemented at the level of direct teaching and at the school level. Students should receive guidance that adapts the education process to their individual characteristics and aspirations as much as possible.