Fortunately, many international laws prohibit child sexual abuse imagery (CSAI) and these laws have been used by industry leaders to make it much harder to find such content on the Internet. However, sexual exploitation of children often begins with content that doesn’t cross the lines drawn by the law, but is still exploitative and deeply disturbing. Depictions showing children in an unnatural, sexually suggestive posture are spread throughout the Internet and are easy to find. This content damages children’s dignity and privacy. There is also a risk that proliferation of this content normalises the sexualisation of minors and makes people think it is an everyday occurrence. The workshop will address how collaboration of stakeholders from industry, government, research and the welfare sector can set the scene for combating and condemnation of such content. Light will be shed on the so called "Grey Areas of (legal) sexual exploitation of children, and countermeasures will be discussed. Bringing together technical knowledge and analytical research expertise on the one hand with the victim's and perpetrator's perspective on the other will design a new approach to fighting CSAI. Artificial intelligence can be of tremendous value for understanding the concepts of provision of CSAI and posing imagery and comprehending the search strategies of perpetrators regards such imagery. In addition knowledge regards commercial transactions and cash flows will help to develop a strategy of combating and condemnation of CSAI in a broad understanding, i. e. covering also the "Grey Area" of (legal) child sexual exploitation.