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Integrating OfficeScan with Office 365 hosted email service

    • Updated:
    • 17 Oct 2016
    • Product/Version:
    • OfficeScan 10.6
    • OfficeScan 11.0
    • OfficeScan XG.All
    • Platform:
    • Windows 2003 Enterprise
    • Windows 2003 Enterprise 64-bit
    • Windows 2003 Server R2
    • Windows 2003 Standard
    • Windows 2003 Standard 64-bit
    • Windows 2008 Enterprise
    • Windows 2008 Enterprise 64-bit
    • Windows 2008 Server R2 Enterprise
    • Windows 2008 Standard
    • Windows 2008 Standard 64-bit
    • Windows 2012 Enterprise
    • Windows 2012 Standard
    • Windows 2012 Standard R2
Summary

You want to migrate the mail service from a traditional on-premise model to a hosted service such as Microsoft Office 365. The Office 365 requires Transport Layer Security (TLS) for Client SMTP Submission to provide a secured communication.

However, OfficeScan currently supports SSL, but not TLS. Thus, you cannot integrate their OfficeScan notifications to the hosted Office 365 mail service.

Details
Public

To resolve this compatibility issue, implement the Simple Mail Transfer Protocol (SMTP) relay and check the configuration afterwards.

  1. Add the SMTP Server feature.
    1. Go to Start > Administrative Tools > Server Manager.
    2. Click Features and select Add Features.
    3. Select SMTP Server.
    4. Select also the Internet Information Services (IIS) Management Console and IIS 6 Management Console features if these are not yet installed.
  2. Start the SMTP service in services.msc and change the startup type to "Automatic".
  3. Open the IIS 6.0 Manager and expand the hostname.
  4. Right-click [SMTP Virtual Server #1] and select Properties.
  5. Navigate to General tab > IP Address > Advanced.
  6. Click Add and select the IP address of the server.
  7. On the TCP port field, type "587" and click OK.

    TCP port field

  8. On the General tab, select the actual IP address of the server from the IP address drop-down list.

    IP address drop-down list

  9. Go to Access tab > Authentication.
  10. Make sure that the Anonymous access check box is ticked and click OK.

    Anonymous access

  11. On the Access tab, click Connection.
  12. Mark the Only the list below radio button and add the IP address of the OSCE server.

    Connection > Only the list below

  13. On the Access tab, select Relay.
  14. Mark the Only the list below radio button and add the IP address of the OSCE server.

    Relay > Only the list below

  15. Go to Delivery tab > Outbound Security.
  16. Select the Basic authentication radio button.
  17. Enter the User name and Password of the Office 365 account which will be used to send emails.
  18. Tick the TLS encryption check box.

    TLS encryption

  19. On the Delivery tab, select Outbound Connections and change the TCP port to 587.

  20. Go to the Delivery tab > Advanced.
  21. On the Smart host field, type "smtp.office365.com" or the URL indicated by the client (e.g. podxxxxx.outlook.com).

    Outbound Connection

After the procedure above, the relay is now configured. To check if netstat -a if 0.0.0.0:587 is listening:

  1. Open a Notepad and type the following:

    FROM: <source email address>
    TO: <destination email address>
    SUBJECT: Test email
    This is a test email sent from my SMTP server

  2. Name this file as Email.txt and save it in C:\InetPub\MailRoot\Pickup.
  3. After a few minutes, check if the file is automatically moved to C:\InetPub\MailRoot\Queue folder. When the SMTP server delivers the mail, the file is automatically deleted from the local server.
  4. If you received the test mail in Office 365, the relay is working.
    If the SMTP server cannot deliver the message, use the non-delivery report (NDR), which is created under the C:\InetPub\MailRoot\BadMail folder, to diagnose the delivery issues.

To configure OfficeScan to send emails via relay:

  1. On the OfficeScan web console, navigate to Administration > Notifications > General Settings.
  2. Enter the following information:

    SMTP server: IP_ADDRESS of the relay
    Port: 587
    From: Email address of the Office 365 (e.g. test@mailbox_office365.com)

  3. Save the settings.
  4. Go to IIS Manager and select the OfficeScan site.
  5. Open the SMTP email feature and mark the Store e-mail in pickup directory radio button.
  6. Set the path of the pickup directory (e.g. C:\InetPub\MailRoot\Pickup) and click Apply.
  7. Test the notification by creating an Eicar test in one of the OfficeScan-protected machines.
Premium
Internal
Rating:
Category:
Configure
Solution Id:
1105919
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