Hopefully the update in 16.19 fixes things.
Updated feature: Encryption updates in Outlook for Mac and Outlook for Windows
MC165252
Stay Informed
Published On : November 16, 2018
We are updating the way to encrypt emails in Outlook for Mac and bringing a consistent approach in the ribbon for both Secure/Multipurpose Internet Mail Extension (S/MIME) and information rights management (IRM). This functionality is now under a new command for Office 365 organizations in both Outlook for Mac and Outlook for Windows. This feature has begun rolling out to all Office 365 organizations. This message is associated with Microsoft 365 Roadmap ID: https://www.microsoft.com/microsoft-365/roadmap?filters=&featureid=32646.
How does this affect me?
The existing Security button in the Outlook for Mac ribbon will become an Encrypt button in version 16.19.18110915+. Similarly, the current Permission button in Outlook for Windows will soon become an Encrypt button. The new Encrypt button will look like a padlock on the ribbon and this lock icon image will appear on all encrypted emails, visible within the Outlook message list. Additionally, Outlook for Mac users will have an additional Encrypt-Only method to secure emails with Office 365 Message Encryption . This means that in addition to supporting S/MIME, which is also currently supported in Outlook on the Web and Outlook for Windows, the Outlook for Mac Encrypt command may include options such as Office 365 Message Encryption Encrypt-Only or Do Not Forward, S/MIME encryption (if configured) and other admin-defined Rights Management Service (RMS) protection templates. Further, the S/MIME sign option in Outlook for Mac will now be consistent with Outlook for Windows under a stand-alone Sign button for digital signing.
What do I need to do to prepare for this change?
There is nothing you need to do to prepare for this change. See Additional information to learn more.