A communication session with a communication endpoint is established. The communication session is placed on hold. For example, the communication session is placed on hold by being sent to a contact center queue. In response to placing the communication session on hold, a message is sent to the communication endpoint that indicates the communication session has been placed on hold. In response to the message, the communication endpoint may initiate a second media stream, such as to play personal media while the communication session is on hold. The second media stream may be a local media file or a remote media file, such as an internet radio station. In response to determining that the communication session is taken off hold, a second message is sent to the communication endpoint to stop playing the personalized media. This process allows the user to play personalized media while being placed on hold.