Technologies to provide a gateway-assisted out-of-band (OOB) remote management session between a remote management service (RMS) and a managed client system are provided. In response to a fault being detected at a client computer system, a RMS receives a client initiated remote access (CIRA) packet from the client system. The CIRA packet includes client configuration information and a single hop network appliance identifier (SHNAI) associated with a network appliance that is a single hop away from the client system. The RMS inspects the SHNAI and the client configuration information, and identifies and copies suitable application(s) from a storage system to a local storage of the gateway indicated by the SHNAI. The RMS instructs/controls the client system to perform an IDE redirection to the gateway in order to provision the application(s) from the local storage of the gateway. Other embodiments may be described and/or claimed.