Hello Nathan Grossenbach,
Thank you for reaching out to Microsoft Q&A Forum!
Since the Report Message / Report Phish add-in shows but the Report button itself is greyed out in New Outlook, Classic Outlook, and Outlook on the web, the issue is usually tied to how the add-in is configured in the tenant, specifically the “User submissions” policy and the “Warn me before reporting” option.
Here are the steps to check:
1. Verify User Submissions policy in Microsoft 365 Security & Compliance
- Go to Microsoft 365 Defender portal: https://security.microsoft.com/reportsubmission
- Confirm that the User submissions policy is enabled and configured to allow reporting for Phish, Junk, and Not Junk.
- If the policy is set to “Warn me before reporting”, make sure the reporting action isn’t blocked, some environments need the warning turned off for the button to become clickable.
2. Check add-in deployment settings
- In the Microsoft 365 admin center > Integrated apps, review the deployment of the Report Message and/or Report Phishing add-in.
- Make sure the correct users/groups are targeted and the add-in is up to date.
- If both add-ins are deployed, remove duplication, keep only Report Message or Report Phishing to avoid conflicts.
3. Client-side cache/updates
- In Outlook desktop, clear the cache: File > Options > Add-ins > COM Add-ins > Go… → disable, restart Outlook, re-enable.
- Make sure New Outlook and Office apps are fully up to date.
4. Workaround confirmation
As you noticed, disabling “Warn Me” makes the button work. That’s because the warning prompt is controlled by the User submissions policy, if misconfigured, it blocks the button.
- If reporting is critical, either leave Warn Me disabled, or adjust the policy in Defender so the warning integrates properly without disabling the action.
Thanks for your precious time and understanding. Please feel free to let me know how it goes. Take care!
Warm regards
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