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This article examines the types of syntactic mitigators employed in directive head acts in familiar letters written during the Spanish Colonial period (sixteenth and early seventeenth centuries). In addition to analysis of the head-act-internal verbal modifiers used in Early Modern Spanish epistolaries, a primary focus of this paper is the question of where the language used in these letters falls on the oral–literate continuum. The directive speech acts noted in the corpus are categorized according to Koike’s (1992) hierarchy of illocutionary force and analyzed using Brown and Levinson’s (1987) theory of face mitigation. The results reveal that the directives issued differ greatly in both nature and structure from those seen in studies of modern (spoken) Spanish as well as those noted in literary corpora of early varieties of the language. A general caution is therefore issued regarding the treatment of letters as manifestations of language that approximates orality.