A system and machine-implemented method for automated communication is presented. Outbound communication time window groups associated with one or more ranges of time valid are identified for initiating an outbound communication. A set of outbound communication time window groups for each of which the current time is within its associated ranges of time is identified. Subsequently, a call record associated with one of the outbound communication time window groups in the set is obtained, and an outbound communication session is initiated to a communication address included in the obtained call record. After an outbound communication session is established, it may be transferred to a live agent. If the outbound communication session has failed however, another outbound communication session may be initiated to the communication address within a later time range.