We present a method to maximize feature matching performance across stereo image pairs by varying illumination. We perform matching between views per lighting condition, finding unique SIFT correspondences for each condition. These feature matches are then collected together into a single set, selecting those features which present the highest quality match. Instead of capturing each view under each illumination, we approximate lighting changes with a pretrained relighting convo- lutional neural network which only requires each view captured under a single specified lighting condition. We then collect the best of these feature matches over all lighting conditions offered by the relighting network. We further present an optimization to limit the number of lighting conditions evaluated to gain a specified number of matches. Our method is evaluated on a set of indoor scenes excluded from training the network with comparison to features extracted from pretrained VGG16. Our method offers an average 5.5× improvement in number of correct matches while retaining similar precision than by the original lit image pair per scene alone.