Long before the East India Company’s founding, individual Europeans traveled to India as soldiers. Rulers recruited such men to gain access to new technical knowledge and to demonstrate their cosmopolitan reach. Company officials had long sought to make use of these adventurers as informal diplomatic agents, but had little success until the mid-eighteenth century, when the Company’s expanding political power made such connections valuable to European adventurers. As the balance of power between the Company and Indian states shifted, those adventurers demanded more formal positions within the Company, including as political residents through whom the Company asserted indirect influence over nominally independent states. Their success in implanting themselves as Company agents contrasts with the status of Indian officers and sepoys employed by the Company, who were also active in the fluid military labor markets of India. Rather than seeing such figures as potential representatives, Company officials used their growing corps of diplomat-adventurers to compel Indian states into new treaties criminalizing such movement and thus curtailing the fluidity of South India’s military economy.