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This study analyzes requests made via email and voicemail for properties of politeness (Brown & Levinson, 1987). Voicemail users have less control over planning, composing, editing, and executing messages, and must manage more nonverbal cues than email users. Thus, it is predicted that email will enable users to create more polite speech than voicemail. A 2 (communication medium: email or voicemail) x 2 (imposition: low or high) factorial design was implemented to test this hypothesis. One hundred fifty-one participants created request messages that were subsequently analyzed for properties of politeness. Overall, the results indicate email requests were more polite than voicemail requests. These results are consistent with the hyperpersonal model (Walther, 1996).