Various technologies for sharing digital images within an instant messaging (IM) session between two users. In one implementation, a first user uploads a set of images to the second user. The set of images may be displayed as thumbnails on the displays of both users. By clicking on one of the thumbnails, either user may make the associated image appear as a larger image on both users' displays. In the event that both users click on different images simultaneously, or near-simultaneously, a protocol may be employed that selects which image is displayed.