Techniques are provided for performing automated operations in order to predict obstacles to mobile device travel paths. Historical mobile device path data about multiple historical paths previously taken by a plurality of mobile devices during a first period of time is tracked. Recent mobile device path data about a plurality of recent paths taken by multiple mobile devices during a second period of time is received and analyzed, including comparing the historical mobile device path data with the recent mobile device path data. Based at least in part on such analysis, a location is predicted for a new obstacle that is determined to be substantially adjacent to one or more of the recent paths. An indication of the predicted location of the new obstacle is provided to one or more user devices.