Drawing on primary materials from the English East India Company (EIC) archives in the British Library (London, UK), this article investigates the early diplomatic encounters between England and Vietnam (Tonkin and Cochinchina) in the seventeenth century. Previous studies have mostly focused on the English trade in Vietnam in that period and their diplomatic missions from the late eighteenth century to 1858 but partly neglected their diplomacy in their first connections with Vietnam (1614–1705). This article thus investigates how the EIC adapted its gift-giving diplomacy to the diverse and shifting political landscape of the Tonkin and Cochinchina kingdoms. While the Trịnh Lords in Tonkin severely limited diplomatic and trade exchanges with EIC agents and other European traders, the Nguyễn Lords in Cochinchina welcomed relations with EIC representatives as it served their ambition to facilitate trade and establish military alliances with other powerful actors in the region.