Not common within the art historical record of the Canadian Military, the work of a number of visual artists participating in the Canadian Forces Artists Program demonstrates a keen and growing interest in portraiture. In this article, the work of Gertrude Kearns, Mary Kavanagh, and Erin Riley will be highlighted to illustrate the recent trend. Their work is contrasted with one another as well as with portraiture created by Canada’s war artists in the First and Second World Wars to bring to light the tensions of representation inherent in military portraiture. It will be shown that shifting perceptions found in the wider employment of portraiture and freedom given to participants in the Canadian Forces most recent official art program have encouraged depictions of members at all levels of the Canadian Forces.