Abstract: A callback window for initiating an electronic communication session with a customer communication endpoint is received. A request from an agent communication endpoint is received to not handle any electronic communication sessions during a time period. For example, a contact center agent may want to take a lunch break. A determination is made that the callback window (or a portion of the callback window) is within the time period. In response to determining the callback window is within the time period, the system may take various steps, such as, automatically denying the request, automatically adjusting the time period, and sending various messages to the agent communication endpoint to identify ways to handle the communication session.