In 1856, Anna Mary Howitt, a London-based artist, began drawing the occult under the mediumistic-artistic name of ‘Comfort’. In this chapter, I depart from Howitt’s spiritual identity as ‘Comfort’ to explore the extent to which her illustrations of communications with spiritual realms address the idea of finding comfort through navigation of darkness. Howitt’s drawings of her spiritual encounters provide a combination of natural elements, religious imagery and female figures; while early drawings were produced through continuous application of grey pencil onto the paper, later depictions present vibrant explosions of colour applied in minute detail. I propose a reading of these images of female spirituality as symbols of Howitt’s navigation of her femininity, influence and creativity. This chapter brings Howitt’s spiritual drawings to light by considering the relevance of her artworks not only for Howitt’s own personal and artistic journey navigating the darkness she found in communicating with the occult, but also for our understanding of intersections between spiritualism, womanhood and creativity in the nineteenth century.