Many children from rural communities in India seeking an education are first-generation learners. These children at times find it difficult to cope with the school environment and learning the state language, which is unfamiliar to them. The parents of these children have no academic background or formal education at any level, which leaves them at a disadvantage as a significant part of their educational process occurs at home. This research is an attempt to study and understand the problems that are being faced by first-generation learners and to assist them in achieving their educational goals. The study uses a qualitative and flexible case-study approach, reflecting the real-life complexities of first generation learners. A flexible design with semi-structured interview method has been employed to allow for more freedom during data collection. This provides an opportunity to present the account of the journey and to refine and modify the original plan to follow up issues that emerged during the process of data collection. It is hoped that the study will provide some insight into the educational needs of first-generation learners and influence future school improvement programmes of both governmental and non-governmental rural development organisation.