The iART project team announces the first iART Workshop in Hannover on 01. and 02. October 2019. The aim of the workshop is to discuss the possibilities of automatic indexing and interactive search of images based on machine learning and artificial intelligence (AI) algorithms with experts from the fields of AI, art history, and digital humanities. One focus of the discussion will be the comparability and similarity between different art objects and how these can be modelled with the help of algorithms. In addition, the requirements from the various disciplines will be collected and serve as a basis for the further development of the software-based retrieval tool. During the workshop, various impulse lectures will be held in order to convey the possibility of AI-supported systems on the one hand, and the domain complexity of art historical comparisons on the other hand.