An industrial service device fleet management system implements an organized and easy to use methodology to manage the digital content stored on each of a plurality of portable or stationary devices used in a plant, such as portable maintenance devices, to assure that each of the portable devices receives or implements only the content that it is supposed to have and is upgraded at the appropriate time to include new content, features, etc. The fleet management system includes a memory for storing information related to the fleet of portable or stationary devices including device identifications, device descriptions, end user names and privileges, the current content of each of the portable devices, and templates defining configuration parameters for the portable or stationary devices. The system also includes a content downloader that obtains, stores, and downloads content (such as software and firmware upgrades, additional features, applications, drivers, knowledge articles, etc.) for execution or display in various ones of the portable or stationary devices, includes a content decider module that analyzes when and if various ones of the portable or stationary devices should be provided additional or new content, and includes a notification system that notifies users of the portable or stationary devices of the need to upgrade or provide new content to the portable or stationary devices.