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Securing Email with Cisco Email Security Appliance (SESA)

Detailed Course Outline

Describing the Cisco Email Security Appliance

  • Cisco Email Security Appliance Overview
  • Technology Use Case
  • Cisco Email Security Appliance Data Sheet
  • SMTP Overview
  • Email Pipeline Overview
  • Installation Scenarios
  • Initial Cisco Email Security Appliance Configuration
  • Centralizing Services on a Cisco Content Security Management Appliance (SMA)
  • Release Notes for AsyncOS 11.x

Administering the Cisco Email Security Appliance

  • Distributing Administrative Tasks
  • System Administration
  • Managing and Monitoring Using the Command Line Interface (CLI)
  • Other Tasks in the GUI
  • Advanced Network Configuration
  • Using Email Security Monitor
  • Tracking Messages
  • Logging

Controlling Sender and Recipient Domains

  • Public and Private Listeners
  • Configuring the Gateway to Receive Email
  • Host Access Table Overview
  • Recipient Access Table Overview
  • Configuring Routing and Delivery Features

Controlling Spam with Talos SenderBase and Anti-Spam

  • SenderBase Overview
  • Anti-Spam
  • Managing Graymail
  • Protecting Against Malicious or Undesirable URLs
  • File Reputation Filtering and File Analysis
  • Bounce Verification

Using Anti-Virus and Outbreak Filters

  • Anti-Virus Scanning Overview
  • Sophos Anti-Virus Filtering
  • McAfee Anti-Virus Filtering
  • Configuring the Appliance to Scan for Viruses
  • Outbreak Filters
  • How the Outbreak Filters Feature Works
  • Managing Outbreak Filters

Using Mail Policies

  • Email Security Manager Overview
  • Mail Policies Overview
  • Handling Incoming and Outgoing Messages Differently
  • Matching Users to a Mail Policy
  • Message Splintering
  • Configuring Mail Policies

Using Content Filters

  • Content Filters Overview
  • Content Filter Conditions
  • Content Filter Actions
  • Filter Messages Based on Content
  • Text Resources Overview
  • Using and Testing the Content Dictionaries Filter Rules
  • Understanding Text Resources
  • Text Resource Management
  • Using Text Resources

Using Message Filters to Enforce Email Policies

  • Message Filters Overview
  • Components of a Message Filter
  • Message Filter Processing
  • Message Filter Rules
  • Message Filter Actions
  • Attachment Scanning
  • Examples of Attachment Scanning Message Filters
  • Using the CLI to Manage Message Filters
  • Message Filter Examples
  • Configuring Scan Behavior

Preventing Data Loss

  • Overview of the Data Loss Prevention (DLP) Scanning Process
  • Setting Up Data Loss Prevention
  • Policies for Data Loss Prevention
  • Message Actions
  • Updating the DLP Engine and Content Matching Classifiers

Using LDAP

  • Overview of LDAP
  • Working with LDAP
  • Using LDAP Queries
  • Authenticating End-Users of the Spam Quarantine
  • Configuring External LDAP Authentication for Users
  • Testing Servers and Queries
  • Using LDAP for Directory Harvest Attack Prevention
  • Spam Quarantine Alias Consolidation Queries
  • Validating Recipients Using an SMTP Server

SMTP Session Authentication

  • Configuring AsyncOS for SMTP Authentication
  • Authenticating SMTP Sessions Using Client Certificates
  • Checking the Validity of a Client Certificate
  • Authenticating User Using LDAP Directory
  • Authenticating SMTP Connection Over Transport Layer Security (TLS) Using a Client Certificate
  • Establishing a TLS Connection from the Appliance
  • Updating a List of Revoked Certificates

Email Authentication

  • Email Authentication Overview
  • Configuring DomainKeys and DomainKeys Identified MailDKIM) Signing
  • Verifying Incoming Messages Using DKIM
  • Overview of Sender Policy FrameworkSPF) and SIDF Verification
  • Domain-based Message Authentication Reporting and Conformance (DMARC) Verification
  • Forged Email Detection

Email Encryption

  • Overview of Cisco Email Encryption
  • Encrypting Messages
  • Determining Which Messages to Encrypt
  • Inserting Encryption Headers into Messages
  • Encrypting Communication with Other Message Transfer Agents (MTAs)
  • Working with Certificates
  • Managing Lists of Certificate Authorities
  • Enabling TLS on a Listener’s Host Access Table (HAT)
  • Enabling TLS and Certificate Verification on Delivery
  • Secure/Multipurpose Internet Mail Extensions (S/MIME) Security Services

Using System Quarantines and Delivery Methods

  • Describing Quarantines
  • Spam Quarantine
  • Setting Up the Centralized Spam Quarantine
  • Using Safelists and Blocklists to Control Email Delivery Based on Sender
  • Configuring Spam Management Features for End Users
  • Managing Messages in the Spam Quarantine
  • Policy, Virus, and Outbreak Quarantines
  • Managing Policy, Virus, and Outbreak Quarantines
  • Working with Messages in Policy, Virus, or Outbreak Quarantines
  • Delivery Methods

Centralized Management Using Clusters

  • Overview of Centralized Management Using Clusters
  • Cluster Organization
  • Creating and Joining a Cluster
  • Managing Clusters
  • Cluster Communication
  • Loading a Configuration in Clustered Appliances
  • Best Practices

Testing and Troubleshooting

  • Debugging Mail Flow Using Test Messages: Trace
  • Using the Listener to Test the Appliance
  • Troubleshooting the Network
  • Troubleshooting the Listener
  • Troubleshooting Email Delivery
  • Troubleshooting Performance
  • Web Interface Appearance and Rendering Issues
  • Responding to Alerts
  • Troubleshooting Hardware Issues
  • Working with Technical Support

References

  • Model Specifications for Large Enterprises
  • Model Specifications for Midsize Enterprises and Small-to-Midsize Enterprises or Branch Offices
  • Cisco Email Security Appliance Model Specifications for Virtual Appliances
  • Packages and Licenses

Lab Outline

  • Verify and Test Cisco ESA Configuration
  • Perform Basic Administration
  • Advanced Malware in Attachments (Macro Detection)
  • Protect Against Malicious or Undesirable URLs Beneath Shortened URLs
  • Protect Against Malicious or Undesirable URLs Inside Attachments
  • Intelligently Handle Unscannable Messages
  • Leverage AMP Cloud Intelligence Via Pre-Classification Enhancement
  • Integrate Cisco ESA with AMP Console
  • Prevent Threats with Anti-Virus Protection
  • Applying Content and Outbreak Filters
  • Configure Attachment Scanning
  • Configure Outbound Data Loss Prevention
  • Integrate Cisco ESA with LDAP and Enable the LDAP Accept Query
  • DomainKeys Identified Mail (DKIM)
  • Sender Policy Framework (SPF)
  • Forged Email Detection
  • Configure the Cisco SMA for Tracking and Reporting