A starting point for this chapter is that children’s literature can be a source of reflection and can encourage children to think critically about technology. In contrast to many textbooks and non-fiction books, fictional stories reflect the complexities and contradictions inherent in technology and at the same time reveal its less obvious and concealed aspects and messages. By using books with a strong story line, which are of interest to children, technology can be presented as part of the world around them. Children’s literature can thus be seen as a mediator of values and attitudes, which makes it an interesting subject matter for Design and Technology education. This chapter involves an exploration of critical aspects of technology found within a selection of children’s books. The stories originate from different historical and cultural contexts, and the basis for the selection is that it represents a variety of critiques and aspects of technology found in children’s literature. The conclusion of the analysis is that children’s literature can contribute to making technology and the nature of technology more comprehensible and visible to pupils. The ambiguous messages in the books reveal the multifaceted and complex nature of technology and make it possible to problematise it in ways textbooks seldom can. As the stories form the basis for critical discussion about the nature of technology, they could also help to broaden perspectives, thereby acting as a pedagogic tool in fulfilling the aims of Design and Technology education.