In accordance with particular embodiments, a computer-implemented method for execution by one or more processors includes intercepting a communication comprising a message. The method also includes identifying words from within the message. The method further includes storing in a dictionary words from within the message of the communication and one or more parameters of the communication for each of the words. The dictionary comprises a plurality of words from a plurality of intercepted text-based communications. The method also includes receiving an encrypted file that is configured to be decrypted using a password. The method additionally includes identifying words from the dictionary to be used to attempt to decrypt the encrypted file. The identified words are identified based on at least one parameter associated with the encrypted file and the one or more parameters stored in the dictionary. The method further includes attempting to decrypt the encrypted file using at least a portion of the identified words from the dictionary as the password for decrypting the encrypted attachment.