The late eighteenth and early nineteenth centuries are now seen as a moment when the ‘second’ British Empire arose from the ruins of the ‘first’ one. One witness to, and participant in, the convulsions of the age was Warren Hastings (1732–1818), the first governor-general of Bengal. Hastings’ career in India, his trial in parliament, and his imperial afterlife all have received fulsome attention. Yet his retirement years have been overlooked, owing to the misperception that they were uneventful. This article introduces and presents a series of letters written by Hastings, late in life, to Governor-General Lord Moira. These letters, published here for the first time, show that Hastings remained an astute observer of British Indian politics. They provide a rich account of the ways in which Britain’s Indian empire evolved in the decades around 1800. Moreover, they reveal that one of that empire’s founders expressed a profoundly critical view of its progress.