Personal portable items are subject to potential loss or misplacement by their owners or authorized users. A system and method is operative with personal portable items which are locally associated with a processor, memory, and sensors (either built-in or via attached sensing device). The memory stores environmental parameters which indicate a potential chance or possibility that an item may be lost, stolen, or misplaced in the near-term, proximate future. The stored parameters are customized to the historical or expected uses of the portable item by a particular user or owner in particular, user-specific contexts. The sensors sense the environment of the portable item in real-time. If the sensed environment or sensed item usage matches the environmental parameters which indicate risk of loss or misplacement, an alert element signals the portable item's user, enabling the user to take anticipatory action to prevent item loss. In an embodiment, at least one first portable item of two or more portable items which are both intended to be substantially on-person of an authorized user, is configured to monitor a status of a second other portable item with which it is paired. If the first portable item detects an anomalous status of the second portable item, the first portable item alerts the authorized user that the second item is at risk of being lost, misplaced, or stolen.