1. Module 6 Planning and Deploying Messaging Security

2. Module Overview Designing Message Security Designing Antivirus and Anti-Spam Solutions

3. Lesson 1: Designing Message Security Defining Message Security Requirements Designing Restrictions to Message Flow Designing SMTP Connector Security Designing Secure Message Routing Between Partner Organizations Designing Client-Based Messaging Security

4. Defining Message Security Requirements Is confidential business information sent by using e- mail? Is private customer information sent by using e- mail? Are recipients and senders internal, or is e-mail sent externally? Are confidential e-mails sent primarily to a limited number of external organizations, or to a variety of recipients? If e-mail is secured using policies or technical solutions, analyze the effectiveness and satisfaction with the solution To collect information required to analyze message recipients and senders, ask: To collect information required to analyze e-mail message contents, ask:

5. Designing Restrictions to Message Flow Transport rules can restrict message flow or modify message contents for messages in transit Restrict message flow with transport rules Implement Hub Transport rules Implement Edge Transport rules Implement message classifications

6. Designing SMTP Connector Security Configure authentication for SMTP Receive connectors Configure authentication for SMTP Send connectors TLS SMTP connector Options for providing additional security for SMTP e-mail:

7. Designing Secure Message Routing Between Partner Organizations Generate a request for TLS certificates on the Edge Transport server 1 1 Configure outbound Domain Security 3 3 Configure inbound Domain Security 4 4 Test Domain-secured mail flow 5 5 Import and enable the certificate on the Edge Transport server 2 2 Domain Security uses TLS with mutual authentication to provide session-based authentication and encryption To set up partner security:

8. Designing Client-Based Messaging Security Exchange servers S/MIME encrypted S/MIME provides message-level authentication, non- repudiation, data integrity, and message encryption AD RMS is a technology that works with RMS-aware applications to help protect documents and e-mail from unauthorized use

9. Lesson 2: Designing Antivirus and Anti-Spam Solutions Overview of Antivirus and Anti-Spam Solution Requirements Options for Implementing Antivirus and Anti-Spam Solutions in Exchange Server 2010 Designing Anti-Spam Solutions Recommendations for Monitoring the Anti-Spam Solution Designing Antivirus Solutions Managing Antivirus Solutions

10. Overview of Antivirus and Anti-Spam Solution Requirements How often are antivirus and anti-spam filters updated, and are the processes automated? How does the anti-spam solution provide a balance between false positives and reducing as much spam as possible? What options does the solution provide for quarantining potentially malicious messages? What management and monitoring tools does the solution provide? How well does the solution integrate with your current system? Critical factors to consider when evaluating antivirus and anti-spam solutions include:

11. Options for Implementing Antivirus and Anti-Spam Solutions in Exchange Server 2010 Connection filtering Sender filtering Recipient filtering Sender ID Content filtering Sender reputation Attachment filtering Forefront Protection 2010 for Exchange Server Office Outlook Junk e-mail filtering Exchange Server 2010 provides a number of antivirus and anti-spam solutions:

12. Designing Anti-Spam Solutions Consider implementing Edge Transport servers as SMTP gateway servers Configure filter agents to reject messages Scan messages for spam before scanning for viruses Scan for spam at the messaging gateway/Edge Server Implement safelist aggregation Implement automatic anti-spam updates Increase the filtering level over time Scan for spam on the Hub Transport server

13. Recommendations for Monitoring the Anti-Spam Solution Monitor for false positives Monitor for filtering effectiveness Monitor the quarantine mailbox Collect user feedback on the spam filter effectiveness Identify administrators, and provide monitoring tools Establish guidelines regarding when to monitor the system Establish a change control process for modifying spam filters Exchange Server 2010 enables anti-spam stamps to help you diagnose spam-related problems As part of the monitoring process design, you should: As part of the monitoring process, you should:

14. Designing Antivirus Solutions Scan both incoming and outgoing e-mail Strip attachments of certain file types Delete rather than clean infected messages Implement a defense-in-depth approach Consider implementing Forefront Security for Exchange Server

15. Managing Antivirus Solutions Monitor daily statistics Regularly monitor antivirus software sites Automate as many processes as possible Develop clearly defined policies and processes Develop a user education process Consider using Microsoft Exchange Hosted Services

16. Lab: Planning and Deploying Messaging Security Exercise 1: Designing Message Security Exercise 2: Designing Antivirus and Anti-Spam Solutions Exercise 3: Implementing Message Security Logon information Estimated time: 60 minutes

17. Lab Scenario You are a messaging engineer for the A. Datum Corporation, an enterprise-level organization with multiple locations. You have been tasked with undertaking an analysis of the organization’s message security requirements. After you complete the analysis, you must update the necessary documentation. After you have completed the message security analysis, you will investigate the organization’s antivirus and anti-spam requirements, and update the necessary documentation with your planned changes. Finally, you will implement S/MIME within the A. Datum organization, as per the security requirements document.

18. Lab Review In exercise 3, you configured S/MIME by deploying a suitable certificate to all users in the Adatum.com domain. Using this method, could you exchange S/MIME-secured messages with partner organizations? What alternatives could you use instead of S/MIME to secure communications between partner organizations?

19. Module Review and Takeaways Review Questions Best Practices