Abstract: A computing system for authenticating users utilizing an interactive chatbot is provided. The computing system includes a processor in communication with a memory, and the processor programmed to: (i) receive an authorization request message for a transaction initiated by a user, wherein the authorization request message includes transaction data, (ii) retrieve user data associated with the user, (iii) determine, based upon the transaction data and the user data, a risk associated with the transaction, (iv) generate, based upon the risk associated with the transaction, one or more prompts for the user, (v) transmit, via the interactive chatbot, the one or more prompts to the user, (vi) receive user input in response to the one or more prompts, and (vii) embed an authentication indicator into the authorization request message, wherein the authentication indicator indicates whether the user is authenticated based upon the user input.