A computer-implemented system and method are provided for warning a user of a missing attachment to an email. The method may include automatically recognizing a natural language of text of an email and selecting a keyword list from a plurality of keyword lists, based on the recognized natural language. Each keyword list is associated with a respective natural language and includes at least one keyword. At least one of the keyword lists includes a multi-sense keyword having a plurality of senses. A first of the plurality of senses is recognized as referring to an attachment and a second of the plurality of senses is recognized as not referring to an attachment. The text of the email is processed to identify an instance, where present, of a keyword that is in the selected keyword list and, for a keyword which is a multi-sense keyword, at least one sense-related rule is applied to a portion of the text which includes the instance of the multi-sense keyword. Based on the application of the at least one sense-related rule, where the email lacks an attachment, a notification is provided to the user.