I present a statistical-based approach to the part-of-speech guessing problem. I see assigning a part-of-speech, such as Adjective or Noun , as a classification problem. My guessing framework, which relies on automated learning of a language model, is described in detail. The rich feature analysis presented is suitable for linguistic data, such as the ones observed in German. I use a large margin classifier learning algorithm to select relevant features and learn appropriate labelling. The system is evaluated using a German corpus.