The processes leading to school failure and early school leaving are complex and involve multidimensional factors. In Portugal, as in other European countries, in the last decade, several policies, programmes, and practices have been developed to address this issue. This article focuses on a socio-educational practice of the study support type developed within a national programme aimed at social inclusion and educational success located in the community. The data collected through a semi-structured interview and a focus group with socio-educational professionals allowed us to identify how the study support practice is characterised and perceived by these actors. Processes and factors of transformation that occurred in the practice regarding its mode of implementation, conceptual evolution, and specificities were also addressed. Results indicate that the practice promotes improvements in participants’ outcomes such as learning, social behaviour, integration, and autonomy; the construction of a strong and sustained relationship with significant adults from the learning point of view; and the completion of compulsory schooling and studies. Hence, the research findings highlight that participation in the practice leads to transformative processes in the academic pathways of children and young people involved in the practice concerning academic, individual, and social dimensions.