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1 Acknowledgments xv About the Author xvii Introduction xix Part 1 SSH Basics 1 Chapter 1 Overview of SSH 3 Differences between SSH1 and SSH2 4 Various Uses of SSH 5 Security 5 Remote Command Line Execution 7 Remote File Transfer 8 Remote Network Access 10 Secure Management 10 Proxy Services 11 Client/Server Architecture for SSH 12 SSH s Encryption Architecture 13 Basic Miscues with SSH 14 Types of SSH Clients/Servers 14 Basic Setup of SSH 15 OpenSSH 16 Red Hat Linux OpenBSD Windows 2000 Server 19 Commercial SSH 23 OpenBSD 3.1 and Red Hat Linux Windows VShell SSH Server 27 Optimal Uses of SSH 29 Summary 30 vii

2 viii Contents Chapter 2 SSH Servers 31 OpenSSH 32 SSH Communications SSH server 39 SSH Communications SSH Server: Unix 39 General 40 Network 40 Crypto 42 Users 43 User Public Key Authentication 44 Tunneling 46 Authentication 46 Host Restrictions 47 Users Restrictions 48 SSH1 Compatibility 49 Chrooted Environment 50 Subsystem Definitions 50 SSH Communications SSH server: Windows 51 General Settings 52 Network Settings 54 Crypto Settings 56 Users Settings 57 Server Public Key Configuration 60 Server Certificate Configurations 61 Tunneling Configurations 62 Authentication Methods 63 Host Restrictions 64 User Restrictions 65 Subsystem Definitions 67 VanDyke Software s VShell SSH Server 69 General Settings 69 General Host Key 70 General Key Exchanges 71 General Cipher 72 General MAC 73 General Compression 74 Authentication 75 Access Control 77 SFTP Section 78 Triggers 79 Connection Filters 80 Port-Forward Filters 81 Logging 83 Comparison of OpenSSH, SSH Server, and VShell 84 Summary 85

3 ix Chapter 3 Secure Shell Clients 87 Command-Line SSH Clients 88 Windows Installation 89 Unix Installation 89 SSH Client Configuration File 94 General 95 Network 95 Crypto 96 User Public Key Authentication 96 Tunneling 97 SSH1 Compatibility 97 Authentication 98 GUI SSH Clients 98 Windows Installation 98 SSH Communications 99 Profile Settings 100 Global Settings 101 VanDyke Software s SecureCRT 104 PuTTY 110 WinSCP 112 MindTerm 113 MacSSH 116 Summary 116 Chapter 4 Authentication 117 General Options 118 SSH Communications SSH Server (Windows) 118 SSH Communications SSH Server (Unix) 120 VShell SSH Server 121 OpenSSH (Unix and Windows) 122 Passwords 123 Host-Based Authentication 127 Server Authentication 129 Public Keys 131 Creating Keys with OpehSSH 134 How to Use an OpenSSH Key on an OpenSSH Server 135 How to Use an OpenSSH Key on SSH Communications SSH Server 136 How to Use an OpenSSH Key on a VShell SSH Server 137 Creating Keys with SSH Communications SSH Client (Unix and Windows Command Line) 138 How to Use SSH Client Keys with SSH Communications SSH Server 139 How to Use SSH Client Keys with an OpenSSH Server 140 How to Use SSH Client Keys with a VShell SSH Server 140

4 x Contents Creating Keys with SSH Communications (Windows GUI) 142 How to Upload an SSH Client Key Pair to SSH Communications SSH Server 144 How to Upload an SSH Client Key Pair to an OpenSSH Server 145 How to Upload an SSH Client Key Pair to a VShell SSH Server 147 Creating Keys with VanDyke SecureCRT 148 VShell SSH Server 149 OpenSSH 150 SSH Communications SSH Server 151 SSH Agents 152 Summary 153 Chapter 5 SSH Management 155 Network Devices 156 Cisco Routers 157 Cisco Switches 160 Cisco VPN Concentrator 160 Cisco PIX Firewalls 162 Network Appliance Filers 163 Secure Management 164 Management Servers 165 Two-Factor Authentication 167 SOCKS Management 169 SSH: User Restrictions 172 Chroot 172 User Access Controls 173 SSH User Restrictions 175 SSH: Network Access Controls 177 SSH TCP wrappers 177 SSH Connection Filters 179 SSH Host Restrictions 181 Summary 183 Part 2 Remote Access Solutions 185 Chapter 6 SSH Port Forwarding 187 Networking Basics of Port Forwarding for Clients 193 Networking Basics of Port Forwarding for Servers 200 SSH Port Forwarding 201 Local Port Forwarding for SSH Clients 205 Configuration for Command-Line Clients 205 Configuration for SSH Communications GUI SSH Client 207 Configuration for VanDyke Software s Secure CRT 209 Configuration for PuTTY 211 Remote Port Forwarding for SSH Clients 213 Configuration for OpenSSH Client (Unix and Windows) 213 Configuration for SSH Communications Command-Line Client (Unix and Windows) 214

5 xi Configuration for SSH Communications GUI SSH Client (Windows) 214 Configuration for VanDyke Software s SecureCRT 215 Port Forwarding for SSH Servers 217 Configuration for OpenSSH Server (Unix and Windows) 217 Configuration for SSH Communications SSH Server (Unix) 217 Configuration for SSH Communications SSH Server (Windows) 220 Configuration for VanDyke Software s VShell SSH Server 222 Advantages to SSH Port Forwarding 225 Summary 226 Chapter 7 Secure Remote Access 229 Secure with SSH 230 Setting Up the SSH Server 232 Setting Up the SSH Client 232 Setting Up the Client 234 Executing Secure 237 Secure File Transfer (SMB and NFS) with SSH 238 Setting Up the SSH Server 241 Setting Up the SSH Client 241 Setting Up the File Server Clients 243 Executing Secure File Transfer 243 Secure File Sharing with SMB and SSH 244 Secure File Sharing with NFS and SSH 245 Secure Management with SSH 246 Setting Up the SSH Server 248 Setting Up the SSH Client 249 Setting Up the Management Clients 252 Executing Secure Management 252 Secure Management with Windows Terminal Services and SSH 253 Secure Management with VNC and SSH 255 Secure Management with pcanywhere and SSH 257 Secure VPN with SSH (PPP over SSH) 259 PPP Daemon on the Server 260 VPN User and Sudo 261 Client Script 261 Summary 264 Part 3 Protocol Replacement 267 Chapter 8 SSH Versatility 269 Terminal Access 270 Compromising a System with Remote Shell (RSH) 271 Compromising a System with Remote Login (Rlogin) 272 Compromising a System with Remote Execution (Rexec) 273 Why Access via SSH Is Better 274

6 xii Contents File Transfer with Secure File Transfer Protocol (SFTP) 276 SFTP with the OpenSSH SFTP Server 277 Using OpenSSH for Management Purposes 277 Using OpenSSH for File Sharing 278 Authorizing Users with OpenSSH 279 OpenSSH on Windows and Cygdrive 280 SFTP with VanDyke Software VShell 281 Using VShell for Management Purposes 281 Using VShell for File Sharing 282 Authorizing Users with VShell 287 SFTP with SSH Communications SSH Server 287 Using SSH Communications SSH Server for Management Purposes 288 Using SSH Communications SSH Server for File Sharing 289 Authorizing Users with SSH Communications SSH Server 292 Comparison of the Three SFTP Solutions 292 Secure Chat 293 Secure Backups 297 Summary 299 Chapter 9 Proxy Technologies in a Secure Web Environment 301 SSH and SOCKS 302 Dynamic Port Forwarding and SOCKS 310 Secure Web Browsing with SSH 314 SSH via HTTP Proxies 321 Securing Wireless Networks with SSH 323 Securing Wireless with SSH and HTTP Proxies 324 Securing Wireless with SSH and Dynamic Port Forwarding 325 Summary 326 Chapter 10 SSH Case Studies 329 Case Study #1: Secure Remote Access 330 The Problem Situation 330 Business Requirements 330 Configuration 334 SSH Client Configuration 334 SSH Server Configuration 339 Results Checklist 343 Case Study #2: Secure Wireless Connectivity 344 The Problem 344 Business Requirements 344 Configuration 347 SSH Client Configuration 347 SSH Server Configuration 350 Results Checklist 351

7 xiii Case Study #3: Secure File Servers 353 The Problem 353 Business Requirements 353 Configuration 354 SSH Server Configuration 354 SSH Client Configuration 356 Results Checklist 357 Summary 358 Epilogue 359 Index 361

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