EmailSentry™ Free Trial

EmailSentry Free Trial Offer

See About EmailSentry for information about what EmailSentry can do for your organization.

CheckTLS offers a free 30 day trial of our EmailSentry product. Use the trial to see if EmailSentry works as described and if it is a worthwhile addition to your security protections.

EmailSentry is safe. The trial is a Microsoft ClickOnce application. Microsoft says "a ClickOnce application cannot break existing applications" and it can be completely uninistalled with Windows Add/Remove Programs.

If your company uses a proxy to connect to the Internet please Contact Us to arrange the free trial.

Free Trial Installation and SignUp

  1. Exit Outlook
  2. Download the EmailSentry ClickOnce installer.
  3. Choose "Run" to begin the installation
  4. Answer yes to any security or "are you sure" prompts
    • If you see this prompt:

      (click to enlarge)
    • click the More Info text
    • verify that the publisher is SecurEmail LLC:

      (click to enlarge)
    • click the Run Anyway button
  5. When the install completes, start Outlook
  6. If you get a message saying the add-in took to long to start and was disabled, see TimeOut Instructions
  7. Start a new email to
  8. Click the Outlook Send button
  9. The EmailSentry Stop screen will popup:

    If you get this screen instead

    it means your Internet runs through a proxy server.
    Please Contact Us to arrange the free trial.
  10. Click the Enable Trial link above the red line to open The EmailSentry Trial Sign-Up page
  11. Scroll down and fill in the fields
  12. Click Save
  13. The screen should refresh with a message that your Trial License is created
  14. Close the EmailSentry Trial Sign-Up page
  15. Click the Cancel button on the EmailSentry popup
Congratulations! Your Free Trial is ready to use.

Using EmailSentry

Using EmailSentry is simple. Just send your email in Outlook the same as always. As long as every recipient is "safe", your email sends just as it always did. If one or more recipients is not "safe", the EmailSentry Stop popup appears and allows you to choose what to do. If you need an unsafe address to test, use

Real License

The trial installs the production version of EmailSentry in Outlook. The differences between a Trial and a Real License are in the back-ends that EmailSentry utilizes:

Trial Licenses use your Windows USERNAME and COMPUTERNAME to grant access, whereas Real Licenses use a public/private key pair to authenticate.
All Trial Licensees share the same CheckTLS back-end settings, whereas Real Licensees can decide how many and what kinds of tests to run on an email address.
Only Real Licensees can do compliance reporting on their user's usage, and query specific transactions to prove a message was secure long after the fact.

A Real License allows your company to tune EmailSentry to your security requirements, including disabling the "Send Anyway" button, or using it to route "unsafe" emails to a different encryption or delivery system. See EmailSentry Setup for more information.

Real Licensees also have access to compliance reporting. See Sample Usage Report and Sample History Query for more information.

Contact Us with any questions.