A concern across many vocational education systems is the high dropout rate from their programs. This problem is likely to be exacerbated at time of low unemployment rates when employers are less demanding about the certification of skills at the time of employment. This qualitative study examines the factors associated with students leaving early from Initial Vocational Education and Training (IVET) institutions in Estonia. The study analyses the challenges and potential risk factors of IVET early leaving from both the students and staff members points of view. The research participants were 20 Estonian IVET students and 12 staff members from various vocational schools. The study highlights the complex interplay of students' challenges and emphasises the importance of addressing them to promote retention and success in vocational education and training programmes. The study employs the Self-Determination Theory, more specifically, the conceptual frame of basic psychological needs to interpret the data. The results of the research indicate that students at risk are mainly shaped by their primary school experience prior to vocational school, with teachers and peers as the main influencers.