In this paper we first describe the technology of automatic annotation transformation, which is based on the annotation adaptation algorithm (Jiang et al., 2009). It can automatically transform a human-annotated corpus from one annotation guideline to another. We then propose two optimization strategies, iterative training and predict-self reestimation, to further improve the accuracy of annotation guideline transformation. Experiments on Chinese word segmentation show that, the iterative training strategy together with predictself reestimation brings significant improvement over the simple annotation transformation baseline, and leads to classifiers with significantly higher accuracy and several times faster processing than annotation adaptation does. On the Penn Chinese Treebank 5.0, it achieves an F-measure of 98.43%, significantly outperforms previous works although using a single classifier with only local features. 1