Hi Kevin
Thank you for reaching out to Microsoft Q&A forum
As far as I know, this behavior occurs because Outlook may automatically disable the Teams Meeting add‑in due to performance or stability detection, or because the add‑in is removed or no longer applicable after migrating to the new Teams client or the new Outlook experience. As a result, the Teams button may disappear, appear greyed out, or behave inconsistently.
Given the symptoms and Microsoft’s documented behavior, the most reliable approach is to focus on systemic causes rather than repeated reinstalls:
First of all, ensure that:
- Outlook and Teams are both running in the same user context (neither should run as administrator).
- .NET Framework 4.8 and Microsoft Edge WebView2 Runtime are installed, as these are required for the Teams Meeting add-in to function correctly.
- The user is signed in to the Teams desktop client and has a valid Teams license assigned.
When users are migrated from classic Teams to the new Teams client, the Teams Meeting add-in may be removed or fail to reinstall correctly. In such cases, repairing or reinstalling the Teams Meeting add-in via the new Teams client is required.
Additionally, note that the new Outlook for Windows does not use the COM add-in. Instead, Teams meetings are integrated natively via a Teams meeting toggle. Users must be signed in to both Outlook and Teams with the same work or school account and be using the new Teams client.
You can find the detail solution for this kind of issue at LINK
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