A device receives re-routing event data identifying a deviation from a proposed route at a particular location. The device determines, based on the re-routing event data, whether the deviation from the proposed route is a problem deviation or a planned deviation, and associates, based on determining that the deviation from the proposed route is a problem deviation, the particular location with an problematic location tag. The device determines that a route, corresponding to a request for routing information received from a navigation device, includes the particular location, and determines, based on a user profile and the problematic location tag, a particular alert level, of a plurality of alert levels, to associate with the particular location. The device detects a proximity of the navigation device to the particular location, and causes a particular alert corresponding to the particular alert level to be provided via the navigation device.