Systems, methods and computer readable medium are provided for perform a method for content and context aware data classification or a method for content and context aware data security anomaly detection. The method for content and context aware data confidentiality classification includes scanning one or more documents in one or more network data repositories of a computer network and extracting content features and context features of the one or more documents into one or more term frequency-inverse document frequency (TF-IDF) vectors and one or more latent semantic indexing (LSI) vectors. The method further includes classifying the one or more documents into a number of category classifications by machine learning the extracted content features and context features of the one or more documents at a file management platform of the computer network, each of the category classifications being associated with one or more confidentiality classifications.