Abstract: Techniques for generating dynamic challenge questions for use in an authentication process are provided herein. An example computer-implemented method can include outputting a first prompt to a user via a user device interface, wherein the first prompt comprises a first set of information-gathering questions; generating dynamic challenge questions for use in an authentication process, wherein the dynamic challenge questions are generated based on user responses to the first set of information-gathering questions; generating a second prompt in connection with an authentication request, wherein the second prompt is based at least in part on at least one of the dynamic challenge questions; processing a user response to the at least one dynamic challenge question, wherein said processing comprises determining a likelihood that the user response matches an automatically estimated response; and resolving the authentication request based on the processing.