This application is directed to augmenting training data used for vehicle driving modelling. A computer system obtains a first image of a road and identifies a drivable area of the road within the first image. The computer system obtains an image of an object and generates a second image from the first image by overlaying the image of the object over the drivable area. The second image is added to a corpus of training images to be used by a machine learning system to generate a model for facilitating driving of a vehicle (e.g., at least partial autonomously). In some embodiments, the computer system applies machine learning to train a model using the corpus of training images and distributes the model to one or more vehicles. In use, the model processes road images captured by the one or more vehicles to facilitate vehicle driving.