A determination is made that a real-time communication session (e.g., a voice call) between a first agent terminal and a customer communication endpoint has been placed on hold by a first contact center agent. An estimated hold time for the real-time communication is determined, based on a rule, in response to determining that the real-time communication session has been placed on hold. It is determined that the estimated hold time for the real-time communication session has expired. In response to determining that the estimated hold time for the real-time communication session has expired, one or more actions occur. For example, the real-time communication session is automatically transferred to a second agent terminal.