This presentation shares a pilot study to assess the multimodal AI tool LLaVA (Large Language and Vision Assistant) in generating descriptive metadata for digitized photographs. The study focuses on evaluation methods for AI-generated descriptions utilizing structured rubrics, which will assess the accuracy, bias, usability, and overall effectiveness of the AI tool. The presentation will also cover the ethics and best practices of using AI-generated metadata for sensitive content. Attendees will gain insights into practical methods for critically evaluating AI-generated outputs, equipping them with adaptable, relevant assessment techniques that may be useful in various library workflow settings.