Technology is an important part of society and digital history applications aid history educators enter a world where it is no longer acceptable to expect students to learn from outdated modes of technology. Students are exposed to a media-saturated world on a daily basis and therefore the question to ask oneself is not ‘Should technology be used in classrooms?’ but rather ‘How can technology be best utilized to enhance learning?’ In this chapter the author aims to address some of those fundamental questions concerning technology in education from the perspective of the discipline of history. It is through the use of history as a domain of knowledge that the author reviews the discussion and relationship between inquiry-based learning and digital technology in education. The chapter uses the example of a study of a digital history program, about Canada’s participation in World War II through the Dieppe raid of 1942, to dissect the implications and rewards of using technology in the history classroom. The author distinguishes between ‘digital technology’ such as computer or network-based applications, and ‘virtual history’ which explains the study and use of the past through digital technology. He explains in more depth the difference between doing history with technology and the use of the virtual historian and students’ learning. The chapter continues with a discussion of the methodology and findings of the study of Canadians’ participation in the Dieppe raid. The author concludes the chapter with a discussion of the study and its effects on student learning and history education through students’ reactions and comments in three different areas: the use of sources as fact sheets, visuals used as illustrations, and the use of digital natives and ‘foreign’ history.