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Serendipity is a popular word that captures a rich phenomenon with potentially far-reaching implications from a personal to global level. Serendipity is associated with revelations, discoveries, life events, and innovations, both big and small, and the lack of consensus on its definition reflects this breadth of meaning. Serendipity is defined in this research as an unexpected experience prompted by an individual’s valuable interaction with ideas, information, objects, or phenomena. While efforts are being made to facilitate serendipity in digital environments (e.g., websites, databases, search engines), we know very little about the complex interaction between the individual and the environment and what actually facilitates serendipity. In three phases, this thesis investigated how individual differences and environmental factors influence work-related serendipity and how serendipity may be facilitated in digital environments. Phase 1 explored serendipity through semi-structured interviews with 12 professionals and scholars. Based on findings from Phase 1, in Phase 2 a serendipitous digital environment scale to measure how well a digital environment supports serendipity was developed, assessed, and honed though an expert review by eight researchers and a web-based survey of 107 university students. Phase 3 employed a web-based survey of 289 professionals and scholars. Through exploratory factor analysis, the serendipitous digital environment scale was refined and assessed. Using multivariate analyses, relationships were explored between serendipity, the underlying factors of the serendipitous digital environment scale, type of digital …