This study analyses the influence of environmental and individual conditions on the quality and the speed of entrepreneurial re-entries in emerging economies after a business failure. We propose a conceptual framework supported by the institutional economic theory to study the influence of environmental conditions; and human and social capital to study the influence of individuals’ skills, experiences, and relationships. A retrospective multiple case study analysis was designed to test our conceptual model by capturing longitudinal information on occurred events, trajectory, and determinants of twenty re-entrepreneurs. Our results show that the entrepreneurial experience and type of venture influence the accelerating effect of re-entrepreneurship, as well as how environmental conditions moderate the quality and speed of entrepreneurial re-entries. We provoke a discussion and implications for multiple actors involved in the re-entry of entrepreneurs after a business failure.