Previous studies have found a close relationship between exit/failure decisions and entrepreneurial/organisational characteristics. In the same line, entrepreneurship literature has recognised that the context matters in any entrepreneurial process, including “exit,” “failure” or “re-entry.” This manuscript proposes a conceptual framework to identify the elements of the entrepreneurial ecosystem that foster or impede the re-entry into entrepreneurship after a business failure. By reviewing the accumulation of knowledge, we identified the individual, the organisational, and the contextual conditions that influence the trajectory of an individual who decides to re-enter after a business failure. This manuscript provides a better understanding of the critical role of agents involved in the entrepreneurial ecosystem. A provocative discussion and implications emerge for this study in order to reduce individual barriers and unfavourable social norms towards business failure.