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 first message is sent to the communication endpoint that indicates the communication session has been placed on hold. A second message is received from the communication endpoint that indicates that a user of the communication endpoint would like to play personal media while the communication session is on hold. The communication session is later taken off hold. In response to determining that the communication session is taken off hold, a third 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.