A communication endpoint is configured to record content, which may be audio content, video content, and/or other content, and send the recorded content to an endpoint, such as a contact center. In one instance, the communication endpoint initiates content recording upon the detection of an outbound user-initiated request, such as an emergency request, and transmits the recorded content when the communication session has been established. As another example, the communication endpoint may record content in a circular manner such that a latest content corresponding to a predetermined amount of time may be transmitted when the communication session has been established.