A system and method for providing computer-generated contextual data to an end-point during a digital transaction is provided. A method includes receiving a trigger message relating to a digital transaction between a consumer and a second entity. The trigger message includes a consumer identifier uniquely associated with the consumer and transaction details at least including a characteristic associated with the digital transaction. A data message including information based on an evaluation of the transaction details against a consumer-linked transaction matrix is obtained. The consumer-linked transaction matrix is linked to the consumer and includes information relating to the digital transaction. The data message is transmitted to a remote device with which the consumer interacts during pendency of the transaction and is configured to cause the device to output a prompt to the consumer displaying the data message.