At-risk students like those with special educational needs, learning difficulties, or pupils at risk of exclusion frequently struggle in transition from basic to secondary vocational education and training, often due to poor personal, learning and social skills. Therefore, several countries implement transition programs like the choice of profession training (CoPT) in Estonia to support youngsters' readiness to continue their studies. This study aimed to identify how the characteristics of powerful learning environments in vocational education (PoLEVE) appear in CoPT in VET teachers and support specialists' experiences. The deductive thematic analysis of 16 semistructured interviews illuminated the development of learning-, life-, cooperation- and self-determinations skills through adaptive teaching and learning support in a safe and positive learning community. Nevertheless, the results also call for empowering at-risk students to cope independently, supporting their construction of vocational knowledge through reflective dialogue and intellectually challenging problem-solving.