Advanced VMware Security

Course Overview
This course is far more advanced than any typical security course. Students will learn about the security
protocols that administrators utilize to secure their environment and dive head first into the actual
workings of the VMware environment. Students will learn about various threats and how to prevent and
secure the VMware environment from them. It is recommended that students have an in-depth knowledge
of VMware’s ESX/ESXI virtualization environment.
Course Outline
Course Introduction 4m
Course Introduction
Chapter 01 – Primer and Reaffirming Our Knowledge 2h 38m
Primer and Reaffirming Our Knowledge
ESX Networking Components
How Virtual Ethernet Adapters Work
How Virtual Switches Work
VMsafe Overview
Current VMsafe Partners
Virtual Switch vs. Physical Switch
Spanning Tree Protocol Not Needed
Virtual Ports
Uplink Ports
Port Groups
Virtual Switch Correctness
VLANs in VMWare Infrastructure
NIC Teaming
Load Balancing
Failover Configurations
Normal Operation
Connection Fails
Signaling Process – Beaconing
Data Rerouted
Layer 2 Security Features
Forged Transmits
Managing the Virtual Network
Symmetric vs. Asymmetric Encryption
Demo – Security in vSwitches
Demo – Hashes
Digital Signatures
Breaking SSL Traffic
Demo – Lab Environment
Demo – ARP Cache Poison
File System Structure
Starting and Stopping Processes
Interacting with Processes
Accounts and Groups
Password & Shadow File Formats
Accounts and Groups (cont.)
Linux and UNIX Permissions
Demo – Intro to Linux
Set UID Programs
Logs and Auditing
Chapter 01 Review
Chapter 02 – Routing and the Security Design of VMware 1h 21m
Routing and the Security Design of VMware
Security of Routing Data
How Traffic Routes Between VMs on ESX Hosts
Different vSwitches, Same Port Group and VLAN
Same vSwitch, Different Port Group and VLAN
Same vSwitch, Same Port Group and VLAN
Security Design of the VMware Infrastructure Architecture
VMware Infrastructure Architecture and Security Features
Virtualization Layer
CPU Virtualization
Memory Virtualization
Cloud Burst
Virtual Machines
Service Console
Virtual Networking Layer
Virtual Switches
Virtual Switch VLANs
Demo – Using VLAN’s
Major Benefits of Using VLANs
Standard VLAN Tagging
Virtual Ports
Virtual Network Adapters
Virtualized Storage
VMware VirtualCenter
Chapter 02 Review
Chapter 03 – Remote DataStore Security 39m
Remote DataStore Security
ESX / ESXi and Fibre Channel SAN Environment and Addressing
Mask and Zone SAN Resources Appropriately
LUN Masking and Zoning
Fiber Channel
Switch Link
What is FC-SP (Fiber Channel – Security Protocol)?
ESP Over Fiber Channel
Fiber Channel Attacks – The Basics
Steps in Securing Fiber Channel
iSCSI vs. Fiber Channel
ESX / ESXi and iSCSI SAN Environment and Addressing
Hardware vs. Software Initiators
iSCSI Security Features
Secure iSCSI Devices Through Authentication
Demo – Storage Security Settings
IPSec Implementation
Steps in Securing iSCSI
Chapter 03 Review
Chapter 04 – Penetration Testing 101 1h 16m
Penetration Testing 101
What is a Penetration Test
Benefits of a Penetration Test
What Does a Hack Cost You?
Cost of a Hack – Example
Current Issues
Chained Exploit Example
Demo – Gonzalez Indictment
The Evolving Threat
Methodology for Penetration Testing / Ethical Hacking
Penetration Testing Methodologies
Types of Tests
Website Review
Demo – Website Review
Seven Management Errors
Some VMware Issues
Not Just About the Tools
Chapter 04 Review
Chapter 05 – Information Gathering, Scanning and Enumeration 1h 47m
Information Gathering, Scanning and Enumeration
What is the Hacker Wanting to Know?
Methods of Obtaining Information
Maltego GUI
Demo – Maltego
Firecat v1.6.2
Demo – Firecat
FireFox Fully Loaded
Google and Query Operators
Shodan – You Have to be Kidding Me!
Demo – Shodan
Introduction to Port Scanning
Popular Port Scanning Tools
ICMP Disabled
NMAP TCP Connect Scan
TCP Connect Port Scan
Half-open Scan
Firewalled Ports
NMAP and Your VMware Servers
Additional NMAP Scans
Demo – NMAP
UDP Port Scan
Enumeration Overview
Banner Grabbing
Banner Grabbing with Telnet
SuperScan 4 Tool: Banner Grabbing
DNS Enumeration
Zone Transfers
Backtrack DNS Enumeration
Active Directory Enumeration
Null Sessions
Syntax for a Null Session
Viewing Shares
Enumeration with Cain and Abel
NAT Dictionary Attack Tool
Injecting Abel Service
Demo – Cain
Chapter 05 Review
Chapter 06 – Penetration Testing and the Tools of the Trade 1h 29m
Penetration Testing and the Tools of the Trade
Vulnerabilities in Network Services
Vulnerability Scanners
Nessus Report
SAINT – Sample Report
OpenVAS Infrastructure
OpenVAS Client
Demo – OpenVAS
Windows Password Cracking
Syskey Encryption
Cracking Techniques
Rainbow Tables
Disabling Auditing
Clearing the Event log
NTFS Alternate Data Stream
Stream Explorer
Encrypted Tunnels
Port Monitoring Software
The Metasploit Project
Defense in Depth
VASTO Modules
SaintExploit at a Glance
Core Impact Overview
Core Impact
Total Exploits from NVD Included in the Penetration Testing Tool
TCP Stream Re-assembling
ARP Cache Poisoning
ARP Cache Poisoning (Linux)
Cain and Abel
Chapter 06 Review
Chapter 07 – DMZ Virtualization and Common Attack Vectors 52m
DMZ Virtualization and Common Attack Vectors
DMZ Virtualization with VMware Infrastructure
Virtualized DMZ Networks
Three Typical Virtualized DMZ Configurations
Partially Collapsed DMZ with Separate Physical Trust Zones
Partially Collapsed DMZ with Virtual Separation of Trust Zones
Fully Collapsed
Best Practices for Achieving a Secure Virtualized DMZ Deployment
Harden and Isolate the Service Console
Clearly Label Networks for Each Zone within the DMZ
Set Layer 2 Security Options on Virtual Switches
Enforce Separation of Duties
Use ESX Resource Management Capabilities
Regularly Audit Virtualized DMZ Configuration
Common Attack Vectors
How We Understand Fake Certificate Injection to Work
Generic TLS Renegotiation Prefix Injection Vulnerability
Testing for a Renegotiation Vulnerability
Vulnerability Requirements
Generic Example
Patched Server with Disabled Renegotiation
Demo – SSL Renegotiation Test
Schmoo Con 2010: Virtualization Vulnerabilities Found!
Schmoo Con 2010: Timeline
Schmoo Con 2010: Identification
Schmoo Con 2010: Server Log In
Schmoo Con 2010: Server on the Internet
Schmoo Con 2010: Vulnerability
Schmoo Con 2010: Redirection Proxy
Schmoo Con 2010: Vulnerable Versions
Schmoo Con 2010: Gueststealer
Chapter 07 Review
Chapter 08 – Hardening Your ESX Server 3h 2m
Hardening Your ESX Server
Section 1 – Virtual Machines
Secure Virtual Machines as You Would Secure Physical Machines
Disable Unnecessary or Superfluous Functions
Take Advantage of Templates
Prevent Virtual Machines from Taking Over Resources
Isolate Virtual Machine Networks
Example Network Architecture
Arp Cache Poisoning
VM Segmentation
Minimize Use of the vSphere Console
Virtual Machine Files and Settings
Disable Copy and Paste Operations
Limit Data Flow from the Virtual Machine to the Datastore
SetInfo Hazard
Do Not Use Nonpersistent Disks
Ensure Unauthorized Devices are Not Connected
Prevent UnAuthorized Removal or Connection of Devices
Avoid Denial of Service Caused by Virtual Disk Modification Operations
Specify the Guest Operating System Correctly
Verify Proper File Permissions for Virtual Machine Files
Demo – Security on your Virtual Machines
Section 2 – Configuring the ESX/ESXi Host
Configuring the Service Console in ESX
Demo – Control VIC Access
Demo – Service Console Administration
Configure the Firewall for Maximum Security
Demo – Firewall Configuration
Limit the Software and Services Running in the Service Console
Processes Running in SC
Use vSphere Client and vCenter to Administer the Hosts Instead of Service Console
Use a Directory Service for Authentication
Demo – AD Integration
Strictly Control Root Privileges
Control Access to Privileged Capabilities
Demo – SSH Access and SUDO
Establish a Password Policy for Local User Accounts
ESX/Linux User Authentication
Configuring ESX Authentication
ESX Authentication Settings
Reusing Passwords
Configuring Password Complexity
Do Not Manage the Service Console as a Linux Host
Maintain Proper Logging
ESX4 Log File Locations
Maintain Proper Logging (cont.)
ESX Log Files
Establish and Maintain File System Integrity
Secure the SNMP Configuration
Protect Against the Root File System Filling Up
Disable Automatic Mounting of USB Devices
Isolate the Infrastructure-related Networks
Configure Encryption for Communication Between Clients and ESX/ESXi
Label Virtual Networks Clearly
Do Not Create a Default Port Group
Do Not Use Promiscuous Mode on Network Interfaces
Protect Against MAC Address Spoofing
Secure the ESX/ESXi Host Console
Chapter 08 Review
Chapter 09 – Hardening Your ESXi Server 20m
Hardening Your ESXi Server
Differences: VMware ESX vs. ESXi
Differences: VMware ESX and ESXi
Configuring Host-level Management in ESXi
ESXi -Strictly Control Root Privileges
Control Access to Privileged Capabilities ESXi
Control Access to Privileged Capabilities ESXi (cont.)
Maintain Proper Logging – ESXi
Establish and Maintain Configuration File Integrity ESXi
Ensure Secure Access to CIM
Audit or Disable Technical Support Mode
Chapter 09 Review
Chapter 10 – Hardening Your vCenter Server 1h 28m
Hardening Your vCenter Server
Set Up the Windows Host for Virtual Center with Proper Security
Limit Network Connectivity to Virtual Center
Use Proper Security Measures When Configuring the Database for Virtual Center
Enable Full and Secure Use of Certificate-based Encryption
Default Certificates
Replacing Server Certificates

vCenter Log Files and Rotation
Collecting vCenter Log Files
Use VirtualCenter Custom Roles
Document and Monitor Changes to the Configuration
VirtualCenter Add-on Components
VMware Update Manager
VMware Converter Enterprise
VMware Guided Consolidation
General Considerations
Client Components
Verify the Integrity of VI Client
Monitor the Usage of VI Client Instances
Avoid the Use of Plain-Text Passwords
vShield Zones Overview
vShield VM Wall Features
vShield VM Flow Features
Demo – vShield Zones
Chapter 10 Review
Chapter 11 – 3rd Party Mitigation Tools 25m
3rd Party Mitigation Tools
Virtualization: Greater Flexibility, Diminished Control
Making Sense of the Virtualization Security Players
1K View of Players
In-depth Look – Authors Picks HyTrust Appliance
HyTrust Appliance – Key Capabilities (cont.): Unified Access Control
HyTrust Appliance – Key Capabilities (cont.): Policy Management
HyTrust Appliance – Key Capabilities (cont.): Audit-quality Logging
HyTrust Appliance – Key Capabilities (cont.): Hypervisor Hardening
In-depth Look – Authors Picks Catbird
Catbird – Policy-driven Security
Catbird – Continuous Compliance
What’s Missing?
Making Sense of It All
Chapter 11 Review
Course Closure
Total Duration: 15hrs 22m

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