The rise of prominent AI models such as ChatGPT and Stable Diffusion has brought the scale of commercial web scraping to the forefront attention of content creators and researchers. Billions of webpages and images are used to train these models without content creators’ knowledge, sparking extensive criticism and even lawsuits against AI firms. Amidst such debates, licensing is proposed by researchers and legal experts to be a potential approach to mitigate content creators’ concerns and promote more responsible data reuse. However, it remains unclear what specific licensing terms will be effective to mitigate content creators’ concerns and what sociotechnical environments are necessary to facilitate the use of licensing at scale. This workshop will provide a venue for researchers, content creators, and legal experts to answer these questions.