Auto-colourisation is the ill-posed problem of creating a plausible full-colour image from a grey-scale prior. The current state of the art utilises image-to-image Generative Adversarial Networks (GANs). The standard method for training colourisation is reformulating RGB images into a luminance prior and two-channel chrominance supervisory signal. However, progress in auto-colourisation is inherently limited by multiple prerequisite dilemmas, where unsolved problems are mutual prerequisites. This thesis advances the field of colourisation on three fronts: architecture, measures, and data. Changes are recommended to common GAN colourisation architectures. Firstly, removing batch normalisation from the discriminator to allow the discriminator to learn the primary statistics of plausible colour images. Secondly, eliminating the direct L1 loss on the generator as L1 will limit the discovery of the plausible colour manifold. The lack of an objective measure of plausible colourisation necessitates resource-intensive human evaluation and repurposed objective measures from other fields. There is no consensus on the best objective measure due to a knowledge gap regarding how well objective measures model the mean human opinion of plausible colourisation. An extensible data set of human-evaluated colourisations, the Human Evaluated Colourisation Dataset (HECD) is presented. The results from this dataset are compared to the commonly-used objective measures and uncover a poor correlation between the objective measures and mean human opinion. The HECD can assess the future appropriateness of proposed objective measures. An interactive tool supplied with the HECD allows for a first exploration of the space of plausible colourisation. Finally, it will be shown that the luminance channel is not representative of the legacy black-and-white images that will be presented to models when deployed; This leads to out-of-distribution errors in all three channels of the final colour image. A novel technique is proposed to simulate priors that match any black-and-white media for which the spectral response is known.