Previous research has shown that companies can be important vehicles for tackling societal challenges. This can include the development of effective cross-sector partnerships, the design of inclusive supply chains, and the creation of inclusive work environments. However, while prior work tends to assume that solutions to societal challenges can be mapped out a priori, in poverty settings, problems and solutions frequently emerge unexpectedly, and solutions are often a matter of serendipity. This creates an important paradox: how can companies harness unexpected events and prepare themselves for serendipity? Based on a (nested) comparative case study design, we studied EduCorp, a South African organization that offered low-cost quality education programs across Sub-Saharan Africa. We studied four cases of “serendipity gained” and “serendipity lost”, and identified the conditions that allow for the emergence and cultivation of serendipity in poverty contexts. We contribute new theory on how organizations operating in poverty settings can harness unexpected events to tackle societal challenges, and introduce a “pro-active” view of events—both in terms of unexpected negative events that may be anticipated and managed, as well as unexpected positive events that may be triggered.