A portable item reporting device automatically learns a use of a portable item which is selected by an authorized user of the portable item, where the device is configured to be attached to and in substantial collocation with the selected portable item, or to be integrated into the portable item. The portable item reporting device monitors item location, item movement, and/or other environmental factors. The portable item reporting device detects and analyzes environmental data during usage of the portable item by the authorized user, or during user-designated storage of the portable item in a storage location. The device further identifies and/or learns, based on the detected enviromental data, one or more repeated patterns and/or context-determined patterns of usage or physical storage of the user's portable item. The device then stores the past, learned pattern(s) of usage data as indicative of expected and/or normal, future use/storage by the authorized user of the portable item.