Aspects of the disclosure relate to detecting usage issues on enterprise systems and dynamically providing user assistance. In some embodiments, a computing platform may receive, from an automated teller system, user presence information indicating that a user has been detected at an automated teller machine associated with the automated teller system. Subsequently, the computing platform may identify, based on the user presence information received from the automated teller system, that the user has a need for assistance with the automated teller machine associated with the automated teller system. In response to identifying that the user has the need for assistance, the computing platform may generate and send one or more commands directing the automated teller machine associated with the automated teller system to execute one or more automated assistance actions corresponding to the need for assistance.