Hello @Kennedy Rivers
Since the Outlook add-in was working last week and is now greyed out, I would first determine whether the problem affects only that specific add-in or Outlook add-ins in general.
If you're using Classic Outlook, check:
File → Options → Trust Center → Trust Center Settings → Add-ins
Make sure Disable all Application Add-ins isn't enabled.
Also check:
File → Account → Account Privacy → Manage Settings
and verify that Optional connected experiences is enabled. Microsoft notes that disabling connected experiences can make certain Office features unavailable. Microsoft Learn – Connected experiences in Office
Next, check whether the add-in itself has been disabled:
File → Options → Add-ins
At the bottom, review both COM Add-ins and Disabled Items. If the affected add-in appears under Disabled Items, re-enable it and restart Outlook.
I would also test the same mailbox using Outlook on the web. If the add-in works there but remains greyed out in desktop Outlook, that strongly points toward the local Outlook installation, profile, or client configuration rather than a tenant-wide restriction.
Since this started after previously working, also check whether a recent Microsoft 365 Apps update coincides with the issue. You can get the installed build from:
File → Office Account → About Outlook
Could you confirm:
- Are you using Classic Outlook or New Outlook?
- Is only this add-in greyed out, or is Get Add-ins / All Apps also unavailable?
- Does it work in Outlook on the web?
- What Outlook version/build is installed?
Those details should help determine whether this is an add-in-specific issue, an Outlook configuration problem, or a policy/client update issue.
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