Abstract: A system and method to automatically trigger data extraction from a Dealerships Management System (DMS) and transmitting it to an insurance service provider for automatic, real-time, generation of insurance application. Generally, an indicator is generated that a customer needs automobile insurance at a point-of-sale. The indicator causes the automatic extraction of the customer's information from a database. The extracted customer information is transmitted to a remote computer for automatic insurance fulfillment. Upon receiving the customer's information, the remote computer automatically populates the appropriate fields of an insurance application and transmits the insurance application to the customer. Upon approval of the insurance application by the customer, a confirmation of insurance is sent to the customer.