A system for assuring agent connection for outbound calls placed in an automated outbound calling campaign includes an outbound dialing server, a digital data repository coupled to the outbound dialing server, the data repository storing outbound dialing records for automated outbound dialing, and software executing on the outbound dialing server from a non-transitory physical medium, the software providing a first function for determining for a specific outbound dialing record if the connection to a live agent must be an assured connection, a second function for dialing and engaging an agent via an internal call for reservation of the agent, and a third function for bridging the call connections forged between the system and the agent and the system and the outbound party upon answer of the outbound call.