Pasifika people are a youthful population group. It is important therefore that Pasifika youth have opportunities to live fulfilling and satisfying lives where they can achieve their dreams, support themselves and their families and make valuable contributions to their local communities, their country and global communities now and in the future. Government and local city councils have become more proactive in developing strategies that will assist young people to be part of an inclusive economy. One of the key areas identified, is the transitioning of low achieving and disengaged school leavers into further education, skills training or employment. Hence the government's and the councils' shared goals of implementing the Mayors' Taskforce for Jobs in 2007, which is to ensure that all youth between 15-19 years of age are in employment, education, training or other activities that lead to their long-term economic independence and wellbeing (Ministry of Youth Development, 2004). Transition courses provide bridging alternatives for youth transitioning from school to employment. They are designed to provide extra help for students who leave school with low or no qualifications. In some cases youth find themselves out of favour with mainstream education and have been forced to end secondary schooling prematurely. Transition learning gives youth a second chance at education by improving their employment marketability. This research highlights the rich stories of Samoan male youths' transitional journeys. The study discusses the critical factors that have contributed either positively or negatively in their ability to transition successfully into the workplace. Eight Samoan male participants were involved in the study ranging from 18-21 years of age. This research topic has evolved from the researcher's involvement in working with South Auckland Pasifika youth for over four years. Some of these youth have been traumatised by their school experiences and have had to face some enormous barriers when transitioning from school into the work place or further tertiary education. After selecting the topic, research frameworks that would be most appropriate for the research were explored. The researcher shares similar cultural and personal experiences to the participants. The framework for the study is therefore aligned to the values of the researcher. Accordingly, the multi-case study approach has been adopted; as such an approach has the potential to reveal what participants feel is significant. The interpretive paradigm underpins this research. The technique for gathering data was through semiformal in-depth interviewing. During the interviews, the participants had the opportunity to discuss the effects that the transitional courses had on them as learners and as Samoan youth. This method of research is culturally appropriate, as it allowed the depth of voices of these young Samoan people to be heard. The themes that have emerged from the findings reflect the broad categories of literature and research findings in the field of transition. The findings also provide new and insightful information about transitional experiences of Pasifika male youth. The research findings from this study focus on key aspects of programme implementation including; the teacher/student relationship, mentoring, student resiliency and the role of the government in youth transition. The research also evaluates the extent to which the transition course curriculum content supports student knowledge and skills in their current work situation. All participants in the study were generally positive about the courses they attended. They discussed the positives in terms of good tutoring, high degree of team cohesion and relevant meaningful learning experiences. The participants cited the negatives as poor teaching, and the low level of some of the literacy and numeracy activities they were expected to complete. Overall they were far more positive about their transitional learning than they were with learning at secondary school. Most felt prepared for work. The study proposes further research in the area of youth transition. Findings from this study will be disseminated to the appropriate government policy makers, city councils, youth services and tertiary providers through presentations at youth development conferences.