This study combines two novel deterministic methods with a Convolutional Neural Network to develop a machine learning method that is aware of directionality of light in images. The first method detects shadows in terrestrial images by using a sliding-window algorithm that extracts specific hue and value features in an image. The second method interpolates light-sources by utilising a line-algorithm, which detects the direction of light sources in the image. Both of these methods are single-image solutions and employ deterministic methods to calculate the values from the image alone, without the need for illumination-models. They extract real-time geometry from the light source in an image, rather than mapping an illuminationmodel onto the image, which are the only models used today. Finally, those outputs are used to train a Convolutional Neural Network. This displays greater accuracy than previous methods for shadow detection and can predict light source-direction and thus orientation accurately, which is a considerable innovation for an unsupervised CNN. It is significantly faster than the deterministic methods. We also present a reference dataset for the problem of shadow and light direction detection.