The current study explores the multifaceted and entwined structure of constraints and spaces of the possibilities of moving ahead among the Dooms of Jammu, India, where the possibilities of upward mobility through education as a means have been observed. Interviews and detailed case study were done with eight cases. Four overlapping super-ordinate themes developed during the course of study: (a) challenges of different generation learners, (b) lack of different forms of capital, (c) dis-identification from own and emulating others and (d) mushrooming of hybrid and mimic generation. The participants experienced the very process of change and continuity through education in their lives. It is observed that education helped in converting the morphology of their existing structure. Each of the interviewee has some exclusive experiences to share, offering significant insights into their lives, struggles and their conditions. The results indicate that the first-generation learners have to face many obstacles. The study concludes that education gives better results under certain circumstances. The chances of low caste children performing better are higher if the educational institutions run with mixed batches with students belonging to all the sections of the society.