Securing Email with Cisco Email Security Appliance

Securing Email with Cisco Email Security Appliance Course Overview

Learn how to deploy and use Cisco® Email Security Appliance to establish protection for your email systems against phishing, business email compromise and ransomware. Help streamline email security policy management. This hands-on course provides you with the knowledge and skills to implement, troubleshoot, and administer Cisco Email Security Appliance, including key capabilities such as advanced malware protection, spam blocking, anti-virus protection, outbreak filtering, encryption, quarantines, and data loss prevention.

Skills Gained

After completing this course you should be able to:

• • Describe and administer the Cisco Email Security Appliance (ESA)

• • Control sender and recipient domains

• • Control spam with Talos SenderBase and anti-spam

• • Use anti-virus and outbreak filters

• • Use mail policies

• • Use content filters

• • Use message filters to enforce email policies

• • Prevent data loss

• • Perform LDAP queries

• • Authenticate Simple Mail Transfer Protocol (SMTP) sessions

• • Authenticate email

• • Encrypt email

• • Use system quarantines and delivery methods

• • Perform centralized management using clusters

• • Test and troubleshoot

Who will the Course Benefit?

Individuals responsible for the deployment, administration and troubleshooting of a Cisco Email Security Appliance.

Requirements

Attendees should meet the following prerequisites:

• • TCP/IP services, including Domain Name System (DNS), Secure Shell (SSH), FTP, Simple Network Management Protocol (SNMP), HTTP, and HTTPS

• • Experience with IP routing

• It is recommended that you have one of the following:

• • Cisco certification (Cisco CCNA® certification or higher)

• • Relevant industry certification, such as (ISC)2, CompTIA Security+, EC-Council, Global Information Assurance Certification (GIAC), and ISACA

• • Cisco Networking Academy letter of completion (CCNA® 1 and CCNA 2)

• • Windows expertise: Microsoft [Microsoft Specialist, Microsoft Certified Solutions Associate (MCSA), Microsoft Certified Systems Engineer (MCSE)], CompTIA (A+, Network+, Server+)

NOTE: Course technical content is subject to change without notice.

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Course Contents

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

Labs



• 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