This article investigates a relatively underdeveloped subject in natural language processing---the generation of punctuation marks. From a theoretical perspective, we study 16 Chinese punctuation marks as defined in the Chinese national standard of punctuation usage, and categorize these punctuation marks into three different types according to their syntactic properties. We implement a three-tier maximum entropy model incorporating linguistically-motivated features for generating the commonly used Chinese punctuation marks in unpunctuated sentences output by a surface realizer. Furthermore, we present a method to automatically extract cue words indicating sentence-final punctuation marks as a specialized feature to construct a more precise model. Evaluating on the Penn Chinese Treebank data, the MaxEnt model achieves an f -score of 79.83% for punctuation insertion and 74.61% for punctuation restoration using gold data input, 79.50% for insertion and 73.32% for restoration using parser-based imperfect input. The experiments show that the MaxEnt model significantly outperforms a baseline 5-gram language model that scores 54.99% for punctuation insertion and 52.01% for restoration. We show that our results are not far from human performance on the same task with human insertion f -scores in the range of 81-87% and human restoration in the range of 71-82%. Finally, a manual error analysis of the generation output shows that close to 40% of the mismatched punctuation marks do in fact result in acceptable choices, a fact obscured in the automatic string-matching based evaluation scores.