Ensure delivery of your phishing tests with PhishProof Direct-to-Inbox. By integrating directly with your Microsoft 365 environment, this feature bypasses traditional security email gateways, ensuring your simulated messages always reach their target for more effective training. 

PhishProof Direct-to-Inbox currently integrates only with Microsoft 365. 

To configure Direct-to-Inbox:

1. From within iLMS, click PhishProof from the left menu
2. Once PhishProof opens, hover over Settings in the left menu, and select Direct-to-Inbox

Step 1: Configure Microsoft 365 for PhishProof

To configure DTI, you must complete several processes within your Microsoft 365 environment, including configuring an inbound connector, mail flow rules, and a connection filter policy, which will allow PhishProof to bypass your email security.

Before starting, ensure you have administrative access to the Microsoft 365 Exchange Admin Center and Microsoft Defender.

Configure an Inbound Connector in Microsoft 365

Configuring an inbound connector in Microsoft 365 Exchange Admin Center streamlines email flow and enhances security for your organization's communication infrastructure. This process allows you to establish trusted connections with partner organizations and implement custom mail routing rules. 

3. In a second browser tab, log in to the Microsoft 365 Exchange Admin Center
4. Navigate to the Mail Flow > Connectors section
5. Click Add Connector

6. Select Partner Organization in the connection type
7. Provide a descriptive Connector Name

8. On the Authenticating sent email screen, select By verifying that the IP address of the sending server matches one of the following IP addresses, which belong to your partner organization
   1. In this case, we (VIPRE Security Group) are your partner organization
   2. Use the relevant IP addresses below based on your geographical location

9. Click Next
10. On the Security Restrictions screen, enable TLS security restrictions by selecting Reject email messages if they aren't sent over TLS, then click Next
11. After reviewing the connector settings, click Create Connector at the bottom of the page

Configure Mail Flow Rules  

This section explains how to create a mail flow rule in Microsoft 365 to bypass spam filtering for emails sent from specific IP addresses. This rule works by setting the Spam Confidence Level (SCL) to -1, which prevents messages from trusted sources from being sent to the junk or spam folder.

12. Assuming you're still logged in to the Microsoft 365 Exchange Admin Center (EAC), select Mail flow > Rules from the navigation menu
13. Click +Add Rule, then select Create a new rule
14. Enter a descriptive name for your rule
15. Under Apply this rule if, select The sender, then choose IP address is in any of these ranges or exactly matches 

    

16. In the window that appears, enter the trusted IP addresses that you want to allow; these should match the IP addresses configured in your inbound connector, as shown above in Table A - DTI Email Service IP Addresses
17. Click Save
18. Under Do the following, select Modify the message properties, and then choose Set the spam confidence level (SCL)
19. In the pop-up window, select Bypass spam filtering from the dropdown menu
    •  There is no need to change this from the default SCL value
20. Click Save, then Next
    • Rule mode: Select Enforce 
      • This turns the rule on as soon as it's saved
    • Stop processing more rules: Check this box
      • This prevents subsequent rules from overriding this action and potentially marking the email as spam 

        

21. Click Next, review your settings, and then click Finish
22. You will see a confirmation that the rule has been created; click Done
23. On the Rules screen, click the checkbox next to your newly created rule and select Edit at the top
24. Your rule details will appear; click the Settings tab and set Priority to 0
    • This ensures it's applied before any other filtering rules
25. Click Save
26. In the list of Rules, under the Status column, you can see if your rule is Enabled or Disabled
    1. If your rule is disabled, you can enable it by clicking Disabled to open the details pane and use the toggle to enable it
       • Allow a few moments for the rule to become fully active

Configure Connection Filter Policy for Phishing Simulations with VIPRE Integrated Email Security

The following steps provide a straightforward method to configure Microsoft Defender to allow phishing simulation emails from VIPRE's PhishProof platform to be delivered directly to your users. This is achieved by whitelisting the PhishProof Direct-to-Inbox (DTI) IP addresses in your connection filter policy, ensuring your phishing simulations are both effective and uninterrupted.

27. Navigate to the Microsoft 365 Defender portal
28. In the navigation pane on the left, expand the Email & collaboration, then select Policies & rules
29. Choose Threat policies and then find and click on the Anti-spam card
30. On the Anti-spam policies page, select Connection filter policy (Default)
31. A details pane will slide out from the right; click the Edit connection filter policy button
32. In the policy settings, find the section titled Always allow messages from the following IP addresses or address range; in the text box provided, enter all the appropriate regional DTI IP addresses from Table A above
    • Ensure you enter one IP address or IP range per line 

      

27. Leave Turn on safe list unchecked
28. Click Save at the bottom of the pane, then click Close to exit the policy editor

Step 2: Connect PhishProof to Microsoft 365 

After completing the steps above in Microsoft 365, select the tab where you have PhishProof open, and go to Step 2: Connect PhishProof to your Microsoft 365 Environment.

Steps 3 & 4: Test Connection and Enable Direct-to-Inbox

Under Step 3: Test your Connection, you can confirm your setup by sending a test email. This will verify that PhishProof can connect to your mail server and deliver messages directly to the target inbox.

28. Enter your desired test email address in the text field and click Send Test Email
29. If successful, you will see a green confirmation that says “Connection successful. A test email has been sent to the address above.”
    1. To verify this in your test Inbox, look for the email subject Test Email - Connection Verification
30. Once that test has been successfully completed, select the toggle next to Enable Direct-to-Inbox and click Save

Congratulations! Direct-to-Inbox has been successfully configured within PhishProof.