This article is an exploration of what selfies and other images are and do in Not Safe For Work (NSFW) communities on tumblr.com. By analyzing ethnographic and interview data, images and blog outtakes, this article spotlights four kinds of conflicts that arise around how selfies and images are used. These are about: (a) reactions to photo-shopped images, (b) altering other people’s selfies and/or reposting them as your own, (c) misunderstandings from separating text from image (caption-stripping), (d) disrespecting the self-shooters’ way of curating their blogs. Boundary theory as well as concepts of social afterlife of content and assumed trust are used to illuminate that images, including selfies, have significant, yet different meanings to different people and play an important part in creating and maintaining meaningful relationships and communities.