Email Encryption Tokamail Microsoft Outlook

How to Encrypt Email in Microsoft Outlook

We live in a world where information is king. Companies have made fortune monetizing people’s data. 

More than ever, companies shall be concerned about data privacy and put in place processes and tools to protect their employee and customer data records.

As enterprises are shifting to the cloud, and employees working from home, data flows exclusively over the Internet, and as such can be monitored, intercepted, or altered.

In this article, we will focus on email encryption and how to keep your communication private end to end and at rest.

Encryption is the best way to protect a message from interception and potential data breaches

To make this encryption as pain-free as possible, most email providers have some tools to help you. 

TLS vs S/MIME what is the best option?

Communications between an SMTP client and an SMTP server can be secured using SSL/TLS (there are two variants: SMTP over SSL/TLS directly, on a specific port, or TLS initiated via STARTTLS within the SMTP protocol). In both cases, this is transport-level security.

In contrast, S/MIME is about message-level security, where the messages are encrypted (even at rest ie. once received and are sitting in your inbox).

In a nutshell, the two solutions complete each other

TLS is widely available including on Microsoft Outlook and should be enabled by default. 

All paid Microsoft 365 plans come with the option to use the S/MIME protocol on top of it.

To start with S/MIME, you’ll need to run the Outlook desktop app for Microsoft Windows and a digital ID from a qualified certificate authority, such as Comodo or Wisekey.

Looking for a free digital certificate to encrypt your email? Check this out.

Step-by-step guide to encrypt emails on Outlook for Windows.

Email Encryption Tokamail Microsoft Outlook trust center encrypt
Microsoft Outlook Trust Center
  1. Open the “Trust Center” by clicking on “file” in the top-left corner and then selecting “options” 
  2. Go through “file” and “options,” then open the “trust center.”
  3. Go Into the “Trust Center Settings”
  4. Click on “trust center settings” to open the trust center window.
  5. Open the “trust center settings” window.
  6. Click on the “Email Security” Tab
  7. In the new window, go into the “email security” tab.
  8. Find the “email security” tab.
  9. Import a Digital ID
  10. Choose “import/export” under the “digital ID” section and follow the on-screen instructions to add your certificate.
  11. Add your S/MIME certificate to Outlook.
  12. Open the “Settings” Window
  13. Once you’ve imported your certificates, click the “settings” button under the “encrypted email” heading.
  14. Open the encryption “settings” window.
  15. Check That It’s Using S/MIME
  16. It should automatically grab your certificate, but it’s best to check that it’s correct before continuing.
  17. Check that your S/MIME settings are correct.
  18. Check the Boxes in “Encrypted Email”
  19. Make sure you check all the boxes under the “encrypted email” heading so that your emails are encrypted and digitally signed.
  20. Check the boxes so that Outlook encrypts your emails and adds your digital signature.
  21. Check That Your Message Is Encrypted
  22. Now, when you start to compose an email, you can go into “options” and click the “encrypt” button with the lock icon to check that you’re using S/MIME encryption.
  23. When you go to write a message, look for the lock icon.
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