This chapter explains the contextual inquiry, during which researchers explore the context and relevant stakeholders, including the prospective users. It’s aim is to get a good grasp of the context in which the eHealth technology will be used. This chapter explains this and provides examples of concrete methods that can be used to conduct a contextual inquiry in practice. These methods are a stakeholder identification and analysis, desk research, a scoping review of the relevant scientific literature, focus groups, interviews, observations, diary study and log data analysis. The chapter also explains why the contextual inquiry is essential for a good eHealth development process.