The first of the case studies, this chapter examines Loudoun’s tenure as commander-in-chief of the British forces in North America during the French and Indian War. Loudoun was active during the Forty-Five and sought to implement the lessons he learnt from that campaign on another geographical fringe. The chapter challenges his historiographical reputation as obstinate, hot-headed and bullying in his colonial interactions, arguing that he preferred negotiation inspired by prior experiences and colonial contexts. Investigating the adaptations in logistics, transportation, and irregular warfare instigated by Loudoun as well as key elements of militarisation strategy such as recruitment, military service, and quartering, the chapter argues that Loudoun proved willing to work within the existing frameworks in North America to achieve his objectives. However, his experiences raised questions about the Britishness of the colonists as the commander interpreted their actions as insubordinate and disloyal, leading him to ‘other’ that population and call for imperial reform.