This thesis presents three papers focusing on the significance of context in idiosyncratic deals (I-deals)- that is, non-standard, individualised employment arrangements negotiated between employees and their employers. The overarching research aim, evident across all three papers, is the role of contexts in I-deals negotiations and how contexts inform how different actors process and respond to I-deals negotiations. The role of contexts in I-deals negotiations is under-explored in extant I-deals literature. Context is predominantly treated as a universal and unchanging variable, with little consideration given to how contexts may shape why, how, and when I-deals emerge, as well as their outcomes. The three papers in this thesis address these context gaps. Providing a qualitative review and Critical Interpretive Synthesis (CIS) of extant empirical I-deals research, the first paper problematises how context is treated in empirical I-deals research and its implications for the understanding and practice of context in I-deals scholarship. In delineating macro context practice in empirical I-deals research, the existing universalistic, singularistic and descriptive approaches to contexts in I-deals are challenged. The second paper highlights the dynamic and multi-layered nature of context by focusing on the concept of temporality and its impact on the creation of I-deals at different time points. Drawing on evidence from three Nigerian firms in Healthcare, Capital Markets and Advertising, the paper investigates the role of temporal contexts (environmental, social, economic, individual) on I-deals and how organisational actors such as employer agents (supervisors, line managers, human resource managers) and I-dealers (employees who negotiate I-deals), respond to enabling and/or constraining temporal conditions during I-deals. Focusing on I-deals outcomes, the third paper explores the significance of contexts for why I-deals may be successful or unsuccessful and the resulting implications for I-deals contents and forms. Specifically, it investigates the underlying contextual forces shaping employer agents’ I-deals authorisation or decline and the impact on the contents and forms of I-deals observed within firms. Empirical evidence for this study was generated from two firms within Nigeria’s telecoms and law industry. This thesis extends I-deals research by exploring how contexts influence different phases of I-deals negotiations. Practical implications for employer agents and I-dealers are offered, one of which is that organisations experiencing considerable flux in their external environments should anticipate I-deals requests and determine how best to respond in line with their contextual realities