A system for providing an automatic software upgrade assistant for remote elevator monitoring experts using machine learning. The system performs operations that include receiving a request from a requestor to install a software upgrade on a controller of an elevator component, the software upgrade dependent on at least one software program being installed on the controller. It is determined whether the at least one software program is installed on the controller. Based at least in part on determining that the at least one software program is installed on the controller: an elapsed time to complete the installation of the software upgrade on the controller is predicted; and an indication is output to the requestor that the software upgrade is permitted to be installed on the controller and the predicted elapsed time to complete the installation.