While many educators have praised the growth of technology in the history classroom, there is still contradictory evidence as to its ability to help strengthen students' historical understanding. One of the most difficult components of historical understanding for young people to achieve is historical empathy. For this study, Foster & Yeager's (1998) conception of empathy as a four step process helped provide a lens by which to view students' impressions of the Civil War. This study attempted to determine if technology, particularly through the use of an activity known as the WebQuest, could lead students to a strong level of historical understanding. Two classes of eighth grade students completed the WebQuest 'Civil War Personal Journal,' and took on various roles of people living during this conflict. Students worked cooperatively to complete journals before, during, and after the Civil War. Despite student appreciation of the WebQuest structure in the classroom and a general positive attitude toward the technology used, results show a wide range of comprehension and understanding of the assigned roles. This article presents four categories to illustrate different types of historical understanding and offers reasons why some students were not able to achieve the levels of empathy desired by the WebQuest. Suggestions for improving historical understanding with technology in the classroom are also proposed.