This case contains three documents relating to the study of Jacobite military history in seventeenth and eighteenth century Europe. Ranging from a document discussing a massacre committed by the Scottish government, to an encrypted intelligence letter, to a record of the experiences of a German ‘Hessian’ mercenary fighting for the British Crown, each document highlights important aspects of Jacobite military history that are largely atypical of traditional discussions around that topic. Together these documents contextualize the experiences of individuals related to military operations between the British Crown and the Jacobites. They provide examples of how the ramifications of the conflicts affected the everyday lives of those who were involved. For example, the text on the Massacre of Glencoe speaks to the gruesome violence faced by civilians during wartime as well as the marginalization of the Highlanders whose religious, political, and cultural values would see them pushed into the peripheries of British society even if they expressed support for the Crown. The encrypted letter is a document featuring the report of a double agent to his Hanoverian superiors in regard to his infiltration of the Jacobite inner circle. It serves as an example of the secretive nature of the underground intelligence war associated with Jacobitism as individuals were forced to conceal their messages in order to escape harsh repercussions. The letter titled Popular Prejudice provides a unique perspective of a mercenary working with the British army. Sentiments originating from Jacobite-sourced pamphlets caused Hessian mercenaries to face prejudice from their fellows in the British army, highlighting how Hanoverian reputations were negatively affected because of their involvement in the conflict. The military aspect of Jacobite history had significant consequences on the lives of individuals, whether they be German mercenaries in the British army, agents in the subterfuge surrounding Jacobitism, or members of a Highland clan, the conflict reached the lives of many.