The technology disclosed herein enables user participation in a communication session using prerecorded messages. In a particular embodiment, a method includes determining a first context of a first prerecorded message from a user. In real-time during a communication session that exchanges user communications between a plurality of participants, the method includes determining a session context of the user communications and determining that the first context corresponds to the session context preceding a first insertion point in the user communications. The method further includes inserting the first prerecorded message into the user communications at the first insertion point.