Space-based lightning imagers have shown that complex cloud scenes that consist of multiple tall convective features, anvil clouds, and warm boundary cloud layers are illuminated by lightning in many different ways, depending on where the lightning occurs and how energetic it is. Modifications to the optical lightning signals from radiative transfer in the cloud medium can lead to reductions in detection efficiency and location accuracy for these instruments, and can also cause some of the optical signals that are detected to have unexpected spatial energy distributions. In this study, we perform Monte Carlo radiative transfer simulations of optical lightning emissions in clouds with complex three-dimensional geometries to shed some light on the origins of certain irregular radiance patterns that have been recorded from orbit. We show that reflections off nearby cloud faces can explain lightning signals in non-electrified clouds, tall clouds can result in poor optical transmission and suppressed radiances that could lead to missed events, and that particularly favorable viewing conditions can cause otherwise normal lightning to produce a “superbolt” that is orders of magnitude brighter than the same flash seen from a different direction.