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- "Epistulas ad oratorem mittim…
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According to OLD s.v. epistula 1b it appears that the plural can in fact refer to a single letter (suggesting "perh. on anal. of litterae"), but as far as I can see there's nothing saying that it can't be an actual plural either, so "letters" should also be correct. (I just got "We send letters to the orator." rejected and reported it.)