A method for providing proactive driving alerts includes determining a road segment of interest, receiving GPS data and contextual data, and identifying a triggering condition in a vicinity of the segment of interest. The method also includes determining an applicability of the triggering condition to the segment of interest, retrieving an alert threshold corresponding to the triggering condition, and obtaining an action factor correlating to a user's driving behavior. The method further includes determining whether the action factor exceeds the alert threshold and providing a proactive alert related to the triggering condition to the user.