Attempt to Leak Data

Objective: Attempt to leak data out of the organization



Use to your remote desktop connection for the following section

Download the DLP test data

  1. Copy and paste the following link into the browser in your remote desktop:
  2. Optional: Open the downloaded file in notepad to view the sensitive (but entirely fake) contents

Attempt to exfiltrate data using one of the following methods

  • Webmail: Use a personal email service to attach and send the file
  • File sharing: Use a file sharing service such as to share the file
  • Get creative: See if you can find a way to get the file out! (Hint: It’s possible with the current policy)

If you explore your blocked WeTransfer upload under Web Traffic Analytics, you will notice the actual request is blocked under the site. This is because in the backend, WeTransfer uploads your file to Amazon S3.