Categories play a fundamental role in our daily lives and are the basis for decision making in most professions (e.g., intelligence analysis, healthcare, and engineering). Categories are a set of objects or events that have similar features and are grouped together because of their similarity. Many categories are acquired as a child (e.g., tools, fruit) but we continue to learn and apply new categories throughout life. Categories range from concrete (e.g., a set of physical objects like houses, dogs…) to abstract (e.g., political ideologies, movie genres…) and narrow (e.g., rifles) to broad (e.g., weapons). People in a variety of knowledge intensive fields (e.g., analysts, commanders, medical doctors) recognize categories in streams of data and make a decision about how to act (or pass the information to a decision maker). Such a categorization system is important now, especially because of the large amount of information that people need to sift through to do their jobs on a regular basis. When decision support systems (DSSs) are applied to support human decision making by automatically recognizing categories, these systems are often not practical in complex dynamic real world environments. Rule based DSSs are limited because it is difficult to develop and maintain large complex rule sets. Current machine learning based DSSs are sometimes limited because they require data that encompasses all of the possible variations as examples to learn from and necessitate significant effort to develop and maintain this training data. This paper describes a cognitive category learning system that uses machine learning and natural language processing (NLP) techniques to categorize unstructured documents or semi-structured objects, such as emails, which we used in this experiment. Our system uses several methods to do this categorization of emails and then arbitrates the best solution based on the individual classifier results. This result provides a more confident answer with less chance of false positive and false negative outcomes. Our system also generates a metadata topic summary for each document or email.