S/MIME sensitivity options in Outlook

(Originally posted September 14, 2022 By ~ Hitesh Manwar and Murree Gopalakrishnan)

Hi Insiders! We’re Hitesh Manwar and Mouli Gopalakrishnan from the Outlook team. We’re excited to announce that adding S/MIME encryption to your email in Outlook for Windows just got a whole lot easier! Admins can now add a configuration option for their organization that populates the sensitivity drop-down menu with labels.

S/MIME Options in Outlook

Many of you use Secure/Multipurpose Internet Mail Extensions (S/MIME) to send digitally signed and encrypted messages to verify the sender’s identity, increase security, and protect the content of your messages.

Previously, you could set up a custom configuration in Outlook to use S/MIME instead of Rights Management Services (RMS) to encrypt or sign emails using the Azure Information Protection (AIP) client. Users would then go to the Options tab and enforce S/MIME in Outlook.

We’ve made this important feature even easier to use by now giving administrators the ability to add S/MIME options to the sensitivity drop-down menu. No custom configuration required! With these labels, users in your organization can easily encrypt and sign emails with a single click.

How it works

For administrators

1. Make sure your organization has: S/MIME settings work.
2. Click here start Enter the button on the Windows taskbar Powershell In the search box, click: Windows Powershell.
3. Import the Exchange Online Management Module and connect to Security and Compliance PowerShell by connecting to an administrator account.

   Connect to Security and Compliance PowerShell

4. Once the connection is established, you can use: Set Label or New Label Configure existing labels to use S/MIME encryption and signing using commands within PowerShell’s Advanced Settings.

   Example PowerShell command where the sensitivity label GUID is ada3ca38-b2c0-468d-ac5f-656a4e0c4208 and the label is associated with both encryption and signing:

   Assign S/MIME encryption and signature to existing labels

   Once setup is complete, users in your organization will see a label with the GUID “ada3ca38-b2c0-468d-ac5f-656a4e0c4208” under the Sensitivity tab. You should rename these labels to something easily identifiable to avoid user confusion.

For users

Here are the steps to apply an S/MIME label to an email:

1. After the administrator sets up the new label, open the email in Outlook.
2. Go to message Click on the tab sensitivity button.
3. New S/MIME encryption and signing options appear in the drop-down menu alongside other sensitivity labels.

   New Sensitivity Label Dropdown Menu in Outlook

   Whenever you apply one of the labels, message recipients will see a lock pad and/or certificate icon in the upper right corner of the email.

   When applied to an email, a signature and encryption icon will appear.

Known Issues

For administrators

• Watermarking is not content marking. Supported For S/MIME labels.
• When an administrator uses sensitivity labels in their organization, they are given the option to either add a header/footer or a watermark to the emails they send. If S/MIME is also provided as a label option, the header/footer content marking will work, but the watermark will not. Click here to learn more about what sensitivity labels can do..
• Configure visual display by Office application type ${app.WXO} Variable statements in the current text string are not allowed.

For users

• A sender may see multiple content displays when sending, retrieving, and resending a message.

Requirements

• Microsoft 365 E3 or E5 license.
• If S/MIME is already deployed within your organization.

effectiveness

This feature is rolling out to Insiders running Outlook Beta Channel version 2208 (Build 15601.20028) or later for Windows.

Features are released over time to ensure everything works smoothly. They are released slowly to a larger number of Insiders, highlighting features you may not have. Sometimes we remove elements based on your feedback to make them even better. This is rare, but we also have the option to completely remove a feature from the product, even if you, as an Insider, had the opportunity to try it out.

feedback

I’d like to hear from you! Go to: help > feedback Let us know what you think about this feature in Outlook.

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