With AI-generated content becoming widespread across digital platforms, it is important to understand how such content is inspired and produced. This study explores the underexamined task of image regeneration, where a human operator iteratively refines prompts to recreate a specific target image. Unlike typical image generation, regeneration begins with a visual reference. A key challenge is whether existing image similarity metrics (ISMs) align with human judgments and can serve as useful feedback in this process. We conduct a structured user study to evaluate how iterative prompt refinement affects similarity to target images and whether ISMs reflect the improvements perceived by human observers. Our results show that prompt adjustments significantly improve alignment, both subjectively and quantitatively, highlighting the potential of iterative workflows in enhancing generative image quality.