How To Send Secure Email in Microsoft Outlook and Gmail

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If you want to learn how to send secure email in Microsoft Outlook and Gmail, look no further! With our data being increasingly exploited by tech giants for money, hackers and fraudsters keen to steal your information at every opportunity, the need for secure and private means of communication is increasingly critical.

Sending secure email via Outlook and Gmail, as two of the most popular email service providers, is a valuable tool to have. So today, we'll run you through what you need to know in order to send a secure email in both Microsoft Outlook and Gmail. Let's get started.

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How To Send Secure Email in Microsoft Outlook

The best way to send secure email in Microsoft Outlook is via encryption. Encryption changes the email from plain text into a cipher. The recipient of the email will be able to decrypt the cipher, as long as they have the private key. It should be noted that encryption is only available to Microsoft 365 subscribers for Windows desktop clients. In addition, before you can encrypt using S/MIME, you need to add a certificate to the keychain on your computer, and then configure it in Outlook:

  • Under the File menu, select Options > Trust Center > Trust Center Settings.
  • In the left pane, select Email Security.
  • Under Encrypted email, choose Settings.
  • Under Certificates and Algorithms, click Choose and select the S/MIME certificate.
  • Choose OK
  • If you are an Office Insider with Microsoft 365 subscription:
    • In an email message, choose Options, select Encrypt and pick Encrypt with S/MIME option from the drop-down
    • You'll see an Encrypt with S/MIME if you have an S/MIME certificate installed on your computer.
    • For Outlook 2019 and Outlook 2016: In an email message, choose Options, select Permissions.
  • Finish composing your email and then choose Send.

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Once you've done this, to encrypt a single email:

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  • In the message that you want to encrypt, click File > Properties.
  • Click Security Settings, and then tick the Encrypt message contents and attachments box.
  • Compose your message, and then click Send.

If you want to encrypt all your future messages as your default:

  • On the File tab, choose Options >Trust Center > Trust Center Settings.
  • On the Email Security tab, under Encrypted email, select the Encrypt contents and attachments for outgoing messages check box.
  • To change additional settings, such as choosing a specific certificate to use, click Settings.

It's important to note that if you encrypt all your emails, then all your recipients need the digital ID to decipher your messages.

How To Send Secure Email in Gmail

Gmail operates slightly differently, using something called confidential mode. This helps to protect sensitive information. But it won't stop people from taking screenshots or photos of your message. To send emails using confidential mode:

  • On your computer, go to Gmail.
  • Click Compose.
  • At the bottom right of the window, click Turn on confidential mode. If you've already turned on confidential mode for an email, go to the bottom of the email, then click Edit.
  • Set an expiry date and passcode. These settings impact both the message text and any attachments. 
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  • If you choose 'No SMS passcode', recipients using the Gmail app will be able to open it directly. Recipients who don't use Gmail will get emailed a passcode.
  • If you choose 'SMS passcode', recipients will get a passcode by text message. Make sure you enter the recipient's phone number, not your own. They will need this in order to open your email.
  • Click Save.
  • You are then ready to complete your email and send it.

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That's all you need to do to send a secure email via Gmail. It's worth pointing out that this, while marked as "confidential" is not encrypted any more than a regular email you send via Gmail. For S/MIME, you would need to be using a Google Workspace Suite account, which is a paid-for service, and most suitable for organisations, rather than individual users.