In education, retrospection is often used as a method for better understanding emerging trends as documented in many books and articles. In this chapter, the focus is not on a broad description of the history of educational technology but on the interplay between learning theories and technologies. However, neither learning theories nor tools are monolithic phenomena. They are composed of multiple attributes, and they refer to many aspects and facets which render the history of educational technology highly complex. Moreover, evolution in both theory and technology reflects no clear successive breaks or discrete developments—rather, waves of growth and accumulation. When looking closer at learning and technology, it becomes clear that many interactions occur. These interactions will be documented following continuous development after World War II. We do not follow a strict timeline but cluster the critical appraisal in the following observations: (1) evolutions in society and education have influenced the selection and use of learning theories and technologies; (2) learning theories and technologies are situated in a somewhat vague conceptual field; (3) learning theories and technologies are connected and intertwined by information processing and knowledge acquisition; (4) educational technologies shifted learner support from program or instructor control toward more shared and learner control; and (5) learning theories and findings represent a fuzzy mixture of principles and applications. The history reflects an evolution from individual toward community learning, from content-driven learning toward process-driven approaches, from isolated media toward integrated use, from presentation media toward interactive media, from learning settings dependent on place and time toward ubiquitous learning, and from fixed tools toward handheld devices. These developments increasingly confront learners with complexity and challenge their responsibility to become active participants in a learning society.