Methods and apparatuses are described for unstructured computer text is analyzed for masking of confidential information using artificial intelligence. A client device generates a message comprising unstructured computer text including confidential information. A server trains a word embedding model using the unstructured text. The server generates a multidimensional vector for each word in the unstructured text, generates a mapping table comprising a predetermined set of words corresponding to confidential information from the unstructured text, and determines one or more neighboring words in the trained word embedding model using the predetermined set of words. The server updates the mapping table to incorporate the one or more neighboring words and executes rules on the unstructured text that filter out one or more words, and applies the updated mapping table to match words in the updated mapping table with words in the filtered text and mask the matching words in the unstructured text.