Although historians have long recognized the important role which Indians played in the English East India Company’s operations, the focus has usually been on the mechanics of direct rule in ‘British’ India. Yet, the expertise of Indian cultural intermediaries was arguably even more important, as well as more contested, in the context of the Company’s growing political influence over nominally independent Indian kingdoms. This article examines the relationships between the East India Company’s political representatives (Residents) and their Indian secretaries (munshis) at Indian royal courts during a period of dramatic imperial expansion, from 1798 to 1818. The article considers how these relationships were conceptualized and debated by British officials, and reflects on the practical consequences of these relationships for the munshis involved. The tensions surrounding the role of the munshi in Residency business exemplify some of the practical dilemmas posed by the developing system of indirect rule in India, where the Resident had to decide how much responsibility to delegate to Indian experts better versed in courtly norms and practices, while at the same time maintaining his own image of authority and control. Although the Resident-munshi relationship was in many respects mutually beneficial, these relationships nevertheless spawned anxieties about transparency and accountability within the Company itself, as well as exciting resentments at court. Both Residents and munshis were required to negotiate between two political and institutional cultures, but it was the munshi who seems to have borne the brunt of the risks associated with this intermediary position.