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Proofpoint, Inc.

Configuring Office 365 for Proofpoint Essentials

This article explains how to configure Microsoft Office 365 to use Proofpoint Essentials as your email gateway.

What is Microsoft Office 365?

Office 365 is a cloud-based solution from Microsoft which offers email, messaging, security, archiving and other capabilities delivered from Microsoft's worldwide network of cloud data centers. For more information please see: https://products.office.com/en-us/business/office

Before you Start

Before continuing with the provisioning and configuration of the Proofpoint Essentials service, it is recommended that you have the information listed below.

Information needed for configuring Proofpoint Essentials

  • MX record(s) for domain(s) you are configuring

Information needed for configuring office 365

Setup Inbound Mail flow

Proofpoint Essentials is deployed between the customer’s Office 365 environment and the Internet. Inbound mail is routed to Proofpoint Essentials by changing the customer’s MX records. After email is processed by Proofpoint Essentials it is routed to Office 365.

Configure Proofpoint Essentials

Locate your MX record for the domain in Office 365

  1. Sign-In to the Office 365 Admin center.
  2. Click on Setup > Domains.
  3. Click on the domain you wish to manage.
  4. Under Exchange Online, locate the MX row in the table from the Points to address or value column (i.e.,bobsbooksupplies.com.mail.protection.outlook.com)
These values will be necessary when you add your domains to Proofpoint Essentials.

 

Adding domain(s) to Proofpoint Essentials

  1. Sign-in to the Proofpoint Essentials user interface.
  2. Click the Domains tab.
  3. Click on New Domain.
  4. Enter the domain name you wish to configure.
  5. Ensure "Relay" is selected for domain purpose.
  6. Enter the delivery and failover destinations values.
  7. Choose the method you wish to use for domain verification.
  8. Click Verify Now if you wish to verify your domain at this stage or Verify Later.
Each Domain must to be verified before it can be enabled.
  1. Repeat if you are adding more than 1 domain.
The delivery and failover destinations refers to the "points to" values captured in the previous section.

Configure OFFICE 365

By-Pass Spam Filtering in Office 365

  1. Sign-In to the Office 365 Admin portal.
  2. Click on Admin > Exchange

This will launch Exchange Admin Center

  1. Click mail flow > rules.
  2. Click + icon to access the pull down menu.
  3. Select By-pass spam filtering
  4. In the new rule window, complete the required fields:
    • Enter a value for Name (e.g.“By-pass Spam filtering for Proofpoint Essentials”)
    • For “Apply this rule if…” select “The sender...IP address is in any of these ranges or exactly matches
    • Add IP address to the IP address list.
      • Type in the address followed by the + icon
      • Repeat for each IP address
    • Ensure Set the spam confidence level (SCL) to is selected in the Do the following... menu
      • Do the following > Modify the message properities > set the spam confidence level > bypass spam filtering
    • Click Save.

Create Inbound Connector

An inbound connector is used to manage mail traffic between Office 365 and Proofpoint Essentials.

  1. While accessing the Exchange Admin Center, click mail flow then connectors.
  2. Click + to launch control.
  3. For “From” select “Partner Organization”.
  4. For “To” select “Office 365”.
  5. Click Next.
  6. Enter a value for Name (e.g.“Proofpoint Essentials Inbound Connector”).
  7. (Optional) Enter a value for Description (e.g.“Inbound connector for Proofpoint Essentials").
  8. Uncheck the turn it on setting. You will turn this inbound connector on once you are ready to cutover mailflow.
  9. Click Next.
  10. Select Use the sender's IP address.
  11. Click Next.
  12. Click +.
  13. Add IP address to the IP address list.
    • Click +.
    • Type in the address followed by OK.
    • Repeat for each IP address.
  14. Clive Next.
  15. Ensure Reject email messages if they aren't over TLS is checked.
  16. Click Next.
  17. Click Save.

Setup Outbound Mail flow

Proofpoint Essentials is deployed between the customer’s Office 365 environment and the Internet. Outbound mail is routed to Proofpoint Essentials by configuring an outbound mail gateway.

Configure Proofpoint Essentials

Enable Outbound Relaying

  1. Sign-in to the Proofpoint Essentials user interface.
  2. Click the Features tab.
  3. Check Enable Outbound Relaying.
  4. Click Save.

Add Service IP addresses to your Inbound Gateway

  1. While logged into the Proofpoint Essentials user interface, click the Domains tab.
  2. Click Managed Hosted Services.
  3. Choose Office 365.
  4. Click Save.

Configure OFFICE 365

Create Outbound Connector

  1. Sign-In to the O365 365 Admin portal.
  2. Click on Admin > Exchange.

This will launch Exchange Admin Center

  1. Click Mail Flow > Connectors.
  2. Click + to access menu.
  3. For “From” select “Office 365”.
  4. For “To” select “Partner Organization”.
  5. Click Next.
  6. Enter a value for Name (e.g.“Proofpoint Essentials”).
  7. Enter a value for Description (e.g.“Outbound connector for Proofpoint Essentials").
  8. Uncheck the turn it on setting. You will turn this outbound connector on once you are ready to cutover mailflow.
  9. Click Next.
  10. For “When do you want to use this connector?” select “Only when email messages are sent to these domains”.
  11. Click +.
  12. Enter * to specify all domains.
  13. Click OK.
  14. Click Next.
  15. For “How do you want to route email messages?“ select “Route email through these smart hosts”.
  16. Click + and enter your Proofpoint smart host value (i.e., outbound-us1.ppe-hosted.com).
  17. Click Save.
  18. Click Next.
  19. For “How should Office 365 connect to your partner organization's email server?” choose your preferred approach.
    • If you choose “Always use Transport Layer Security (TLS) to secure the connection”, please choose  “Any digital certificate, including self-signed certificates“.
  20. Click Next.
  21. Click Next.
  22. Click + icon and enter an email address for validation.
  23. Click OK.
  24. Click Validate.
  25. Click Save.

If you are using Proofpoint Essentials Email Archive, you will need to create an additional outbound connector. Please refer to: Configuring Journaling for Office 365 for additional steps.

If you are using another archiving service, you will need to create an additional outbound connector to ensure journal emailed is not sent to Proofpoint Essentials. If it is sent to Proofpoint Essentials it will be subject to outbound rate limiting policies. Please contact your archiving service provider for instructions.

 

Update Sender Policy Framework (SPF)

When sending outbound email through the Proofpoint Essentials gateway, recipients receive mail sent from Proofpoint Essentials rather than Office 365 mail servers. If the recipient's mail service attempts to verify that the message came from your domain, it must confirm that the gateway server is an authorized mail server for your domain.

To enable this, you need to add the Proofpoint Essentials SPF record to your domain.

Cutting Over Mailflow

Enable & TEST domain(s)

  1. Sign-in to the Proofpoint Essentials user interface.
  2. Click the Domains tab.
  3. Click the relay control to enable the domain for relay.
Once the domain is turned on, you will need to wait for Proofpoint Essentials MTAs to be updated.This occurs every half-hour. You should not proceed to the next step until you;ve waited for this change to be applied.
  1. Click the test domain (clipboard) icon to verify Proofpoint Essentials can deliver to the specified SMTP destination.

Update YOUR MX records

You will need to add Proofpoint Essentials MX records to your DNS record.

You may want to add the MX records with a low priority ahead of your cutover. Once ready, you can then increase the priority of the Proofpoint Essentials MX records while decreasing the priority of your existing MX record.

Enable INBOUND Connector

  1. Sign-In to the O365 365 Admin portal.
  2. Click on Admin > Exchange.
  3. Click Mail Flow > Connectors.
  4. Select the Inbound Connector and click edit (pencil icon).
  5. Check the turn it on checkbox.
  6. Click Next and move through the next 3 screens.
  7. Click Save.

Enable Outbound Connector

  1. Sign-In to the O365 365 Admin portal.
  2. Click on Admin > Exchange.
  3. Click Mail Flow > Connectors.
  4. Select the outbound connector and click edit (pencil icon).
  5. Check the turn it on checkbox and click next through the remaining screens.
  6. Click Validate.
  7. Click Save.

Enable BY-PASS Spam filtering Rule

  1. While accessing the Exchange Admin Center, click mail flow > rules.
  2. Check the checkbox next to the mail flow rule you created previously.

VERIFY INBOUND MAILFLOW

  1. While logged into the Proofpoint Essentials user interface, click the Logs tab.
  2. Select Any from the Status drop-down and click Search.
  3. Look for new entries to be listed in the search results.

Verify Outbound Mailflow

  1. Send a test message from an Office 365 mailbox to an external SMTP address.
  2. While logged into the Proofpoint Essentials user interface, click the Logs tab.
  3. Select Outbound mail from the type drop-down.
  4. Select Any from the status drop-down and click Search.
  5. Look for the test message that was sent.