Via a qualitative study, we introduce and elucidate 5 layers of context-related job search demands (omnibus, organizational, social, task, and personal) that are encountered by both employed and unemployed job seekers. We develop a process model to portray the mechanisms (managing mood and motivation, feedback/help seeking, and self-reflection/learning) through which these context-related demands are related to several important job search outcomes. We provide new insight into employed job seekers, showing that they report the job search as full of difficulties, obstacles, and challenges, and that some of these demands parallel those that unemployed job seekers face.