A system and method for delivering interactive voice messages using a voice messaging system are disclosed. In an illustrative embodiment, the system comprises a voice messaging processor and memory containing machine readable instructions which, when executed by the processor, enable the voice messaging system to: receive an inbound call from a sender; record an interactive voice message from the sender directed to at least one recipient; receive a voice message retrieval request from a recipient; play the interactive voice message for the recipient; and initiate an interactive session with the recipient to elicit responses from the recipient regarding the interactive voice message. In one aspect of the invention, an application server is provided for generating interactive voicemails and placing the inbound call from the sender to the voice messaging processor.

 
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