Organizations often operate in complex and dynamic environments which place a premium on employees’ ongoing learning and acquisition of new competencies. Additionally, the majority of learning in organizations does not take place in formal training settings, but we know relatively little about how informal field-based learning (IFBL) behaviors relate to changes in job performance. In this study, we first clarified the construct of IFBL as a subset of informal learning. Second, on the basis of this clarified construct definition, we developed a measure of IFBL behaviors and demonstrated its psychometric properties using (a) a sample of subject matter experts who made item content validity judgments and (b) both an Amazon Mechanical Turk sample (N = 400) and a sample of 1,707 healthcare employees. Third, we advanced a grounded theory of IFBL in healthcare, and related it to individuals’ regulatory foci and contextual moderators of IFBL behaviors-job performance relationships using a cross-level design and lagged nonmethod bound measures. Specifically, using a sample of 407 healthcare workers from 49 hospital units, our results suggested that promotion-focused individuals, especially in well-staffed units, readily engage in IFBL behaviors. Additionally, we found that the IFBL-changes in job performance relationship was strengthened to the extent that individuals worked in units with relatively nonpunitive climates. Interestingly, staffing levels had a weakening moderating effect on the positive IFBL-performance improvements relationship. Detailed follow-up analyses revealed that the peculiar effect was attributable to differential relationships from IFBL subdimensions. Implications for future theory building, research, and practice are discussed.