Interactive visual tools designed to facilitate the visual exploration and investigation of emails sent over Secretary Hillary Clinton’s controversial and politically important private email server are presented. These tools are implemented, alongside data extracted from the emails using text processing, in an interactive, public web application at shiny.math.uwaterloo.ca/sas/clinton/ to allow those interested to use their functionality. This functionality is used to view email volumes, keywords, and key people involved in Clinton’s tenure as United States Secretary of State, in particular during the Libyan Civil War in 2011 and her divisive response to the attack on the American embassy in Benghazi. Patterns present, such as email gaps, are examined in light of these events and compared to less controversial times in an attempt to remove personal bias. A clear picture emerges of the conclusions supported by the data and those which cannot be explained.