This study inquires into the difficulties besetting communication via answering machines and ways of dealing with those difficulties. It regards communication from the perspective of conversation analysis and centres both on the pre-recorded texts callers are confronted with and on messages left by callers. It transpires that communication via answering machines is subject to the tensions existing between oral and written language, dialogue and monologue, and interpersonal and mass communication. The complex demands made on both participants produce interesting phenomena related to the acquisition process involved in the use of this medium.