Send & Receive Issues

How to Fix Phish Alert Add-in Disconnecting Outlook When Sending Email

Olivia Miller Sep 28, 2026 870 views

Question details

The user experiences Outlook disconnections when attempting to send emails while the Phish Alert add-in is active.

Fix Phish Alert Add-in Disconnecting Outlook When Sending Emails

Product: Microsoft Outlook
Device & OS: not provided
Scenario: Sending an email with the Phish Alert add-in enabled.
Observed behavior: Outlook disconnects from the server or crashes unexpectedly when the user tries to send an email.

Before you start

Determine whether the Phish Alert add-in you are using is a built-in Microsoft feature or a third-party extension provided by your organization's security vendor.

Solution 1Recommended

Enable Optional Connected Experiences in Outlook

Adjusting your privacy settings to allow connected experiences can resolve connection blocks caused by cloud-dependent add-ins like Phish Alert.

Many security and reporting add-ins require active cloud connections to function properly. If Outlook's privacy settings are restricting these connections, it can cause the client to disconnect when the add-in is triggered during the email sending process.

Open Outlook Options

Launch Microsoft Outlook, click on the 'File' tab in the top left corner, and select 'Options' at the bottom of the menu.

Access Privacy Settings

In the Outlook Options window, navigate to the 'General' tab and click on the 'Privacy Settings' button under the Privacy section.

Enable Connected Experiences

Scroll down to find the 'Optional connected experiences' section. Check the box to enable these features, click 'OK', and restart Outlook before testing the email sending process again.

Enable Optional Connected Experiences in Outlook

Restart Required: Make sure to completely close and reopen Outlook for the new privacy settings to take effect.

Solution 2

Update Outlook and Verify Add-in Configuration

Outdated Microsoft 365 applications or misconfigured Microsoft reporting add-ins can lead to connectivity drops during email dispatch.

Solution 3

Contact the Third-Party Vendor or Microsoft Support

If the add-in is developed by a third party or the issue persists with Microsoft's own add-in, direct support from the vendor may be required.

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Frequently Asked Questions

Why does the Phish Alert add-in cause Outlook to disconnect?

The add-in often requires active cloud connections to verify email content or report phishing attempts. If Outlook's privacy settings block these 'connected experiences', the add-in may fail and cause the email sending process or the client itself to disconnect.

How do I know if my Phish Alert add-in is from Microsoft or a third party?

You can check the add-in details by navigating to File > Manage Add-ins or 'Get Add-ins' in Outlook. Many organizations use third-party tools like KnowBe4, while others use Microsoft's built-in Report Message or Report Phishing add-ins.

Will reinstalling the add-in fix the disconnection issue?

Sometimes. If the add-in's local cache is corrupted, having your IT administrator remove and redeploy the add-in from the Microsoft 365 Admin Center can resolve underlying connectivity glitches.

Outlook & Email Problems