Automatic image annotation automatically labels image content with semantic keywords. For instance, the Relevance Model estimates the joint probability of the keyword and the image [3]. Most of the previous annotation methods assign keywords separately. Recently the correlation between annotated keywords has been used to improve image annotation. However, directly estimating the joint probability of a set of keywords and the unlabeled image is computationally prohibitive. To avoid the computation difficulty we propose a heuristic greedy iterative algorithm to estimate the probability of a keyword subset being the caption of an image. In our approach, the correlations between keywords are analyzed by “Automatic Local Analysis” of text information retrieval. In addition, a new image generation probability estimation method is proposed based on region matching. We demonstrate that our iterative annotation algorithm can incorporate the keyword correlations and the region matching appr...