Today, Artificial Intelligence (AI) is at the forefront of art-historical research and cultural discourse: from the creation of digital images with the use of transformer models, such as Dall-E and Midjourney, to the analysis of large data sets of images with the use of neural networks. Scholarly written analysis is also shifting with the use of ChatGPT and other language models. Now is a critical time for the field of Digital Art History to reflect and respond to the uses and applications of data with these computational methods. While AI inquiry offers many potential avenues for rethinking art historical research, without careful consideration algorithms also risk ethical pitfalls. Though there has been fervent discussion around AI tools intersecting with art production, as well as a long history of tool development for image recognition and analysis, this issue seeks to further the conversation in response to the recent influx of scholarly engagement with AI and art-historical scholarship.