Hi @Matt Moriarty
Welcome to our forum!
As i know, this issue occurs for one or more of the following reasons:
- The user account that's signed in to Outlook isn't a Microsoft 365 subscriber.
- The security labels aren't published in the Microsoft Purview compliance portal.
- The Outlook version doesn't support the built-in labeling.
- The label policy distribution process isn't successful.
Please refer to the article and have a try step-by-step:
Hope it helps!
If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".
Note: Please follow the steps in our [documentation] to enable e-mail notifications if you want to receive the related email notification for this thread.