Serendipity is generally characterized as a sagacious, unsought discovery. Innovations and advances in science and engineering such as penicillin and Teflon as a result of interactions with tangible engineered and natural phenomena are often labeled serendipitous. Serendipity also results from more conceptual interactions with information, knowledge, and ideas. But how does serendipity emerge when the discovery is predominantly conceptual? What conditions in the digital environment would help facilitate less tangible but similarly unexpected and fortunate interactions for knowledge workers? The objective of my research is to approach the study of serendipity as a process involving precipitating conditions, interacting internal and external factors that either hinder or facilitate serendipity, to understand how to best facilitate serendipity in a digital, information-rich environment. This research will contribute to an emerging field of study – support for serendipity in information systems – that is striving to make our experiences in digital environments richer and more meaningful.