The present invention relates to system and method for providing ultra-quick audio/video messaging phonebook and delivery. The system includes an application server communicating with one or more communication devices phonebook application installed therein. The phonebook application configures device to displays all contacts including registered and unregistered contacts available in the memory. When a user selects and holds a contact, application initiates a short duration audio/video messages recording for the selected contact and detect whether the selected contact is a registered contact number or unregistered contact number of phonebook directory application. If selected contact number recognize as a registered contact, application automatically transmits recorded message to the selected contact via application server upon release of hold to contact. If selected contacted recognize as unregistered contact number, application automatically transmits a message containing an unique web link to phonebook directory web portal providing direct web access to recorded audio/video message. The system also provides smart delivery option of audio/video recorded message on recipient's device. The system detects present status of recipient's device based on information received from device sensors and user inputs, for playing audio/video message. In responses to detected status, an audio or visual alert is provided with further possibilities of hands free contextual engagement on the side of the recipient's device.