The automated generation of a unique letter or unique letters using one or more context variables for the letter. The contextual variables may represent author characteristics, audience characteristics, tone, word diversification, letter type, and so forth. Different entropy may be used for each letter to thereby generate a unique letter even if the context for the letters is the same. Nevertheless, each unique letter is suitable for the given context. If desired, the automatically generated letter may be further edited, for example, for grammatical, word choice, or legal content. Thus, the letter may appear to be custom drafted by a human for the context, whereas the letter was entirely or substantially computer-generated.