SSL Remote Access VPNs (Network Security)

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Edition: 1st
Format: Paperback
Pub. Date: 2008-06-10
Publisher(s): Cisco Press
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Summary

SSL Remote Access VPNs An introduction to designing and configuring SSL virtual private networks Jazib Frahim, CCIEreg; No. 5459 Qiang Huang, CCIE No. 4937 Ciscoreg; SSL VPN solutions (formerly known as Cisco WebVPN solutions) give you a flexible and secure way to extend networking resources to virtually any remote user with access to the Internet and a web browser. Remote access based on SSL VPN delivers secure access to network resources by establishing an encrypted tunnel across the Internet using a broadband (cable or DSL) or ISP dialup connection. SSL Remote Access VPNsprovides you with a basic working knowledge of SSL virtual private networks on Cisco SSL VPN-capable devices. Design guidance is provided to assist you in implementing SSL VPN in existing network infrastructures. This includes examining existing hardware and software to determine whether they are SSL VPN capable, providing design recommendations, and guiding you on setting up the Cisco SSL VPN devices. Common deployment scenarios are covered to assist you in deploying an SSL VPN in your network. SSL Remote Access VPNsgives you everything you need to know to understand, design, install, configure, and troubleshoot all the components that make up an effective, secure SSL VPN solution. Jazib Frahim, CCIEreg; No. 5459, is currently working as a technical leader in the Worldwide Security Services Practice of the Cisco Advanced Services for Network Security. He is responsible for guiding customers in the design and implementation of their networks, with a focus on network security. He holds two CCIEs, one in routing and switching and the other in security. Qiang Huang, CCIE No. 4937, is a product manager in the Cisco Campus Switch System Technology Group, focusing on driving the security and intelligent services roadmap for market-leading modular Ethernet switching platforms. During his time at Cisco, Qiang has played an important role in a number of technology groups, including the Cisco TAC security and VPN team, where he was responsible for trouble-shooting complicated customer deployments in security and VPN solutions. Qiang has extensive knowledge of security and VPN technologies and experience in real-life customer deployments. Qiang holds CCIE certifications in routing and switching, security, and ISP Dial. Understand remote access VPN technologies, such as Point-to-Point Tunneling Protocol (PPTP), Internet Protocol Security (IPsec), Layer 2 Forwarding (L2F), Layer 2 Tunneling (L2TP) over IPsec, and SSL VPN Learn about the building blocks of SSL VPN, including cryptographic algorithms and SSL and Transport Layer Security (TLS) Evaluate common design best practices for planning and designing an SSL VPN solution Gain insight into SSL VPN functionality on Cisco Adaptive Security Appliance (ASA) and Cisco IOSreg; routers Install and configure SSL VPNs on Cisco ASA and Cisco IOS routers Manage your SSL VPN deployment using Cisco Security Manager This security book is part of the Cisco Pressreg; Networking Technology Series. Security titles from Cisco Press help networking professionals secure critical data and resources, prevent and mitigate network attacks, and build end-to-end self-defending networks. Category: Networking: Security

Author Biography

Jazib Frahim, CCIE No. 5459, has been with Cisco for more than nine years. Having a bachelor’s degree in computer engineering from Illinois Institute of Technology, he started out as a TAC engineer in the LAN Switching team. He then moved to the TAC Security team, where he acted as a technical leader for the security products. He led a team of 20 engineers in resolving complicated security and VPN technologies. He is currently working as a technical leader in the Worldwide Security Services Practice of Advanced Services for Network Security. He is responsible for guiding customers in the design and implementation of their networks with a focus on network security. He holds two CCIEs, one in routing and switching and the other in security. He has written numerous Cisco online technical documents and has been an active member on the Cisco online forum NetPro. He has presented at Networkers on multiple occasions and has taught many on-site and online courses to Cisco customers, partners, and employees.

 

He has recently received his master of business administration (MBA) degree from North Carolina State University. He is also an author of the following Cisco Press books: Cisco Network Admission Control, Volume II: NAC Deployment and Troubleshooting, and Cisco ASA: All-in-One Firewall, IPS, and VPN Adaptive Security Appliance.

 

Qiang Huang, CCIE No. 4937, is a product manager in the Cisco Systems Campus Switch System Technology Group, focusing on driving the security and intelligent services roadmap for Cisco marketleading modular Ethernet switching platforms. He has been with Cisco for almost ten years. During his time at Cisco, Qiang played an important role in a number of technology groups including the following: technical lead in the Cisco TAC security and VPN team, where he was responsible for troubleshooting complicated customer deployments in security and VPN solutions; a security consulting engineer in the Cisco Advanced Service Group, providing security posture assessment and consulting services to customers; a technical marketing engineer focusing on competitive analysis and market intelligence in network security with specialization in the emerging SSL VPN technology. Qiang has extensive knowledge of security and VPN technologies and experience in real-life customer deployments. Qiang holds CCIE certifications in routing and switching, security, and ISP dial. He is also one of the contributing authors of Internetworking Technologies Handbook, Fourth Edition. Qiang received a master’s degree in electrical engineering from Colorado State University.

 

Table of Contents

Introduction
Introduction to Remote Access VPN Technologies
Remote Access Technologiesp. 5
IPsecp. 5
Software-Based VPN Clientsp. 7
Hardware-Based VPN Clientsp. 7
SSL VPNp. 7
L2TPp. 9
L2TP over IPsecp. 11
PPTPp. 13
Summaryp. 14
SSL VPN Technology
Cryptographic Building Blocks of SSL VPNsp. 17
Hashing and Message Integrity Authenticationp. 17
Hashingp. 18
Message Authentication Codep. 18
Encryptionp. 20
RC4p. 21
DES and 3DESp. 22
AESp. 22
Diffie-Hellmanp. 23
RSA and DSAp. 24
Digital Signatures and Digital Certificationp. 24
Digital Signaturesp. 24
Public Key Infrastructure, Digital Certificates, and Certificationp. 25
SSL and TLSp. 30
SSL and TLS Historyp. 30
SSL Protocols Overviewp. 31
OSI Layer Placement and TCP/IP Protocol Supportp. 31
SSL Record Protocol and Handshake Protocolsp. 33
SSL Connection Setupp. 34
Application Datap. 42
Case Study: SSL Connection Setupp. 43
DTLSp. 48
SSL VPNp. 49
Reverse Proxy Technologyp. 50
URL Manglingp. 52
Content Rewritingp. 53
Port-Forwarding Technologyp. 55
Terminal Servicesp. 58
SSL VPN Tunnel Clientp. 58
Summaryp. 59
Referencesp. 60
SSL VPN Design Considerations
Not All Resource Access Methods Are Equalp. 63
User Authentication and Access Privilege Managementp. 65
User Authenticationp. 66
Choice of Authentication Serversp. 66
AAA Server Scalability and High Availabilityp. 67
AAA Server Scalabilityp. 67
AAA Server High Availability and Resiliencyp. 68
Resource Access Privilege Managementp. 68
Security Considerationsp. 70
Security Threatsp. 71
Lack of Security on Unmanaged Computersp. 71
Data Theftp. 71
Man-in-the-Middle Attacksp. 72
Web Application Attackp. 73
Spread of Viruses, Worms, and Trojans from Remote Computers to the Internal Networkp. 73
Split Tunnelingp. 73
Password Attacksp. 74
Security Risk Mitigationp. 74
Strong User Authentication and Password Policyp. 75
Choose Strong Cryptographic Algorithmsp. 75
Session Timeout and Persistent Sessionsp. 75
Endpoint Security Posture Assessment and Validationp. 75
VPN Session Data Protectionp. 76
Techniques to Prevent Data Theftp. 76
Web Application Firewalls, Intrusion Prevention Systems, and Antivirus and Network Admission Control Technologiesp. 77
Device Placementp. 78
Platform Optionsp. 79
Virtualizationp. 79
High Availabilityp. 80
Performance and Scalabilityp. 81
Summaryp. 82
Referencesp. 82
Cisco SSL VPN Family of Products
Overview of Cisco SSL VPN Product Portfoliop. 85
Cisco ASA 5500 Seriesp. 87
SSL VPN History on Cisco ASAp. 87
SSL VPN Specifications on Cisco ASAp. 88
SSL VPN Licenses on Cisco ASAp. 89
Cisco IOS Routersp. 90
SSL VPN History on Cisco IOS Routersp. 90
SSL VPN Licenses on Cisco IOS Routersp. 90
Summaryp. 91
SSL VPNs on Cisco ASA
SSL VPN Design Considerationsp. 93
SSL VPN Prerequisitesp. 95
SSL VPN Licensesp. 95
Client Operating System and Browser and Software Requirementsp. 96
Infrastructure Requirementsp. 97
Pre-SSL VPN Configuration Guidep. 97
Enrolling Digital Certificates (Recommended)p. 98
Step 1: Configuring a Trustpointp. 98
Step 2: Obtaining a CA Certificatep. 99
Step 3: Obtaining an Identity Certificatep. 100
Setting Up ASDMp. 101
Uploading ASDMp. 102
Setting Up the Appliancep. 103
Accessing ASDMp. 104
Setting Up Tunnel and Group Policiesp. 106
Configuring Group-Policiesp. 107
Configuring a Tunnel Groupp. 110
Setting Up User Authenticationp. 110
Clientless SSL VPN Configuration Guidep. 114
Enabling Clientless SSL VPN on an Interfacep. 116
Configuring SSL VPN Portal Customizationp. 117
Logon Pagep. 118
Portal Pagep. 123
Logout Pagep. 125
Portal Customization and User Groupp. 126
Full Customizationp. 129
Configuring Bookmarksp. 134
Configuring Websitesp. 135
Configuring File Serversp. 137
Applying a Bookmark List to a Group Policyp. 139
Single Sign-Onp. 140
Configuring Web-Type ACLsp. 141
Configuring Application Accessp. 144
Configuring Port Forwardingp. 144
Configuring Smart Tunnelsp. 147
Configuring Client-Server Plug-Insp. 150
AnyConnect VPN Client Configuration Guidep. 152
Loading the SVC Packagep. 154
Defining AnyConnect VPN Client Attributesp. 155
Enabling AnyConnect VPN Client Functionalityp. 155
Defining a Pool of Addressesp. 156
Configuring Traffic Filtersp. 159
Configuring a Tunnel Groupp. 159
Advanced Full Tunnel Featuresp. 159
Split Tunnelingp. 159
DNS and WINS Assignmentp. 161
Keeping the SSL VPN Client Installedp. 162
Configuring DTLSp. 163
Cisco Secure Desktopp. 164
CSD Componentsp. 165
Secure Desktop Managerp. 165
Secure Desktopp. 165
Cache Cleanerp. 166
CSD Requirementsp. 166
Supported Operating Systemsp. 166
User Privilegesp. 167
Supported Internet Browsersp. 167
Internet Browser Settingsp. 167
CSD Architecturep. 168
Configuring CSDp. 169
Loading the CSD Packagep. 169
Defining Prelogin Sequencesp. 170
Host Scanp. 182
Host Scan Modulesp. 183
Basic Host Scanp. 183
Endpoint Assessmentp. 183
Advanced Endpoint Assessmentp. 184
Configuring Host Scanp. 184
Setting Up Basic Host Scanp. 184
Enabling Endpoint Host Scanp. 186
Setting Up an Advanced Endpoint Host Scanp. 187
Dynamic Access Policiesp. 189
DAP Architecturep. 190
DAP Recordsp. 191
DAP Selection Rulesp. 191
DAP Configuration Filep. 191
DAP Sequence of Eventsp. 191
Configuring DAPp. 192
Selecting a AAA Attributep. 193
Selecting Endpoint Attributesp. 195
Defining Access Policiesp. 197
Deployment Scenariosp. 205
AnyConnect Client with CSD and External Authenticationp. 206
Step 1: Set Up CSDp. 207
Step 2: Set Up RADIUS for Authenticationp. 207
Step 3: Configure AnyConnect SSL VPNp. 208
Clientless Connections with DAPp. 209
Step 1: Define Clientless Connectionsp. 210
Step 2: Configuring DAPp. 211
Monitoring and Troubleshooting SSL VPNp. 212
Monitoring SSL VPNp. 212
Troubleshooting SSL VPNp. 215
Troubleshooting SSL Negotiationsp. 215
Troubleshooting AnyConnect Client Issuesp. 215
Troubleshooting Clientless Issuesp. 217
Troubleshooting CSDp. 219
Troubleshooting DAPp. 219
Summaryp. 220
SSL VPNs on Cisco IOS Routers
SSL VPN Design Considerationsp. 223
IOS SSL VPN Prerequisitesp. 225
IOS SSL VPN Configuration Guidep. 226
Configuring Pre-SSL VPN Setupp. 226
Setting Up User Authenticationp. 226
Enrolling Digital Certificates (Recommended)p. 229
Loading SDM (Recommended)p. 232
Initial SSL VPN Configurationp. 235
Step 1: Setting Up an SSL VPN Gatewayp. 237
Step 2: Setting Up an SSL VPN Contextp. 239
Step 3: Configuring SSL VPN Look and Feelp. 241
Step 4: Configuring SSL VPN Group Policiesp. 245
Advanced SSL VPN Featuresp. 247
Configuring Clientless SSL VPNsp. 247
Windows File Sharingp. 253
Configuring Application ACLp. 257
Thin Client SSL VPNsp. 259
Step 1: Defining Port-Forwarding Listsp. 261
Step 2: Mapping Port-Forwarding Lists to a Group Policyp. 262
AnyConnect SSL VPN Clientp. 264
Step 1: Loading the AnyConnect Packagep. 264
Step 2: Defining AnyConnect VPN Client Attributesp. 266
Cisco Secure Desktopp. 276
CSD Componentsp. 277
Secure Desktop Managerp. 277
Secure Desktopp. 277
Cache Cleanerp. 278
CSD Requirementsp. 278
Supported Operating Systemsp. 278
User Privilegesp. 279
Supported Internet Browsersp. 279
Internet Browser Settingsp. 279
CSD Architecturep. 280
Configuring CSDp. 281
Step 1: Loading the CSD Packagep. 282
Step 2: Launching the CSD Packagep. 283
Step 3: Defining Policies for Windows-Based Clientsp. 283
Defining Policies for Windows CEp. 298
Defining Policies for the Mac and Linux Cache Cleanerp. 298
Deployment Scenariosp. 301
Clientless Connections with CSDp. 301
Step 1: User Authentication and DNSp. 302
Step 2: Set Up CSDp. 303
Step 3: Define Clientless Connectionsp. 303
AnyConnect Client and External Authenticationp. 304
Step 1: Set Up RADIUS for Authenticationp. 305
Step 2: Install the AnyConnect SSL VPNp. 306
Step 3: Configure AnyConnect SSL VPN Propertiesp. 306
Monitoring an SSL VPN in Cisco IOSp. 307
Summaryp. 311
Management of SSL VPNs
Multidevice Policy Provisioningp. 314
Device View and Policy Viewp. 314
Device Viewp. 314
Policy Viewp. 318
Use of Common Objects for Multidevice Managementp. 320
Workflow Control and Role-Based Access Controlp. 322
Workflow Controlp. 323
Workflow Modep. 324
Role-Based Administrationp. 326
Native Modep. 326
Cisco Secure ACS Integration Modep. 327
Summaryp. 331
Referencesp. 331
Table of Contents provided by Publisher. All Rights Reserved.

Excerpts

Introduction IntroductionThis book provides a complete guide to the SSL VPN technology and discusses its implementation on Cisco SSL VPN-capable devices. Design guidance is provided to assist you in implementing SSL VPNs in an existing network infrastructure. This includes examining existing hardware and software to determine whether they are SSL VPN capable, providing design recommendations, and guiding you on setting up the Cisco SSL VPN devices.Toward the end of Chapters 5 and 6, common deployment scenarios are covered to assist you in deploying an SSL VPN in your network. Who Should Read This Book?This book serves as a guide for network professionals who want to implement the Cisco SSL VPN remote access solution in their network to allow users to access the corporate resources easily and safely. The book systematically walks you through the product or solution architecture, installation, configuration, deployment, monitoring, and troubleshooting the SSL VPN solution. Any network professional should be able to use this book as a guide to successfully deploy SSL VPN remote access solutions in their network. Requirements include a basic knowledge of TCP/IP and networking, familiarity with Cisco routers/firewalls and their command-line interface (CLI), and a general understanding of the overall SSL VPN solution. How This Book Is OrganizedPart I of this book includes Chapters 1 and 2, which provide an overview of the remote access VPN technologies and introduce the SSL VPN technology. The remainder of the book is divided into two parts.Part II encompasses Chapters 3 and 4 and introduces the Cisco SSL VPN product lines, with guidance on different design considerations.Part III encompasses Chapters 5 through 7 and covers the installation, configuration, deployment, and troubleshooting of the individual components that make up the SSL VPN solution.Part I, "Introduction and Technology Overview," includes the following chapters:Chapter 1, "Introduction to Remote Access VPN Technologies": This chapter covers the remote access Virtual Private Network (VPN) technologies in detail. Protocols, such as the Point-to-Point Tunneling Protocol (PPTP), Internet Protocol Security (IPsec), Layer 2 Forwarding (L2F), Layer 2 Tunneling Protocol (L2TP) over IPsec, and SSL VPN, are discussed to provide readers with an overview of the available remote access VPN technologies.Chapter 2, "SSL VPN Technology": This chapter provides a technology overview of the building blocks of SSL VPNs, including cryptographic algorithms, SSL and Transport Layer Security (TLS), and common SSL VPN technologies.Part II, "SSL VPN Design Considerations and Cisco Solution Overview," includes the following chapters:Chapter 3, "SSL VPN Design Considerations": This chapter discusses the common design best practices for planning and designing an SSL VPN solution.Chapter 4, "Cisco SSL VPN Family of Products": This chapter discusses the SSL VPN functionality on Cisco Adaptive Security Appliance (ASA) and Cisco IOS routers and provides product specifications that are focused on SSL VPNs.Part III, "Deploying Cisco SSL VPN Solutions," includes the following chapters:Chapter 5, "SSL VPNs on Cisco ASA": This chapter provides details about the SSL VPN functionality in Cisco ASA. This chapter discusses clientless and full tunnel SSL VPN client implementations and focuses on Cisco Secure Desktop (CSD). This chapter also discusses the Host Scan feature that is used to collect posture information about end workstations. The dynamic access policy (DAP) feature, its usage, and detailed configuration examples are also provided. To reinforce learning, many different deployment scenarios are presented along with their con

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