Scanning tool for detecting sensitive information in text transmissions

An email scanning tool comprising:

• a keyword database comprising at least one keyword;
• a first plurality of machine instructions comprising initialization instructions that identify an application operator, displays a first graphical user interface (GUI) comprising a status identifier, and checks for a digital signature file;
• a second plurality of machine instructions that generates a second GUI comprising a digital signature reminder, wherein the second plurality of machine instructions are configured to execute when the first plurality of machine instructions does not detect the digital signature file;
• a third plurality of machine instructions comprising tracking database update instructions that records installation or non-installation of the scanning tool to an external database;
• a fourth plurality of machine instructions comprising an email subject line scan function, an email body scan function, and an email attachment scan function, wherein the fourth plurality of machine instructions execute when a user sends an email, wherein the email subject line scan function searches for the at least one keyword within an email subject line, wherein the email body scan function searches for the at least one keyword within an email body, wherein the email attachment scan function searches for the at least one keyword within an email attachment and the filename of the email attachment.