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Next Generation SSH2 Implementation : Securing Data in Motion

Max Caceres, Aaron E. Earle, Devin Ganger, Wipul Jayawickrama, Jan Kanclirz Jr., Dane Liu, Tim Robichaux, Eric S. Seagren, Brad Smith, Christopher Stokes

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New security risks, continuously evolving regulation and increasing security standards have created new and growing needs for secure internal information transfers, which SSH provides. This book addresses these new trends in depth, offering the most up-to-date information on the integration of SSH into a security environment. It covers the newest features and applications of SSH-2 (which received Proposed Standard status from the IETF in 2006). SSH2 is more secure than previous versions and has many expanded uses on a wider variety of computing platforms. Another particular note driving new SSH2 adoption are the requirements of recent legislation (PCI/HIPAA/SOX/FISMA). SSH 2 has become an even more valuable tool, as it provides communications security compliance with the latest standards.This book offers the most up-to-date information on SSH2 in a practical, hands-on, tutorial-style reference that goes well beyond UNIX implementation. It concentrates on the latest version of SSH 2 with all new information. * Discover why SSH2 offers more robust security than SSH1 and how to incorporate it into your network administration software toolbox. cover......Page 1 Copyright......Page 2 Lead Author and Technical Editor......Page 3 Contributing Authors......Page 4 Acknowledgments......Page 9 Introduction......Page 10 Why Is There a Need To Use SSH?......Page 11 What SSH Does and Does Not Do......Page 13 Comparison Between SSH and SSHv2......Page 14 Encryption Standards......Page 15 What Is SCP and SFTP?......Page 16 SSH and the C-I-A Triad......Page 17 Comparison Between SSH and SSHv2......Page 20 SSH and the C-I-A Triad......Page 21 Frequently Asked Questions......Page 22 OSI Model and Then Some......Page 23 50,000 Foot View of the OSI Model......Page 24 Application Layer (7)......Page 26 Presentation Layer (6)......Page 27 Transport Layer (4)......Page 28 Network Layer (3)......Page 29 Physical Layer (1)......Page 30 Using the OSI Model to Troubleshoot......Page 31 Applying the OSI Model to Forensics......Page 37 Using the OSI Model to Troubleshoot......Page 45 Applying the OSI Model to Forensics......Page 46 Frequently Asked Questions......Page 47 An Introduction To Cryptography......Page 49 Confidentiality......Page 50 Integrity......Page 51 Authentication......Page 52 Secure Sockets Layer/Transport Layer Security......Page 53 Cryptographic Systems......Page 54 Symmetric Key Cryptosystems......Page 56 Asymmetric Key Cryptosystems......Page 57 Block Ciphers......Page 58 Stream Ciphers......Page 59 Cryptographic Key Management......Page 60 Diffie–Hellman Key Exchange Protocol......Page 61 Cryptographic Hash Functions......Page 62 Message Authentication Codes......Page 63 Attacks on Cryptosystems......Page 64 Ciphertext-Based Attacks......Page 65 SSH Key Exchange......Page 66 Encryption Algorithms Supported by SSH......Page 67 Cryptographic Protocols and Applications......Page 68 Cryptographic Functions......Page 69 Cryptography and SSH......Page 70 Frequently Asked Questions......Page 71 SSH Features......Page 73 Introduction to SSH......Page 74 SSH Standards......Page 75 SSH Message Types......Page 77 SSH-TRANS......Page 78 SSH-USERAUTH......Page 79 SSH-CONNECT......Page 81 SSH vs. Telnet/Rlogin......Page 85 SSH Client/Server Overview......Page 87 Packet Capture Detection......Page 88 Summary......Page 91 SSH Standards......Page 92 Packet Capture Detection......Page 93 Frequently Asked Questions......Page 94 SSH Shortcomings......Page 95 Getting the Request to the Target: Physical Attack......Page 96 Attacking in person......Page 97 Attacking the Psyche......Page 98 Phishing......Page 99 Hardware......Page 100 Trojans......Page 101 How Do You Know if You’re Under an SE Attack?......Page 102 Responding to an SE Event......Page 103 IT Responses......Page 104 Management Response......Page 105 What’s Currently Working?......Page 106 Actually Looking at the Browser Training......Page 108 Policy and Procedures for SE Attack......Page 109 You’re So Wonderful!......Page 111 Please Help Me Save My Job!......Page 112 Responding to an SE Event......Page 113 Defending against Social Engineering Attacks......Page 114 Frequently Asked Questions......Page 115 SSH Client Basics......Page 117 Using OpenSSH to Encrypt Network Traffic Between Two Hosts......Page 118 The OpenSSH Suite......Page 119 Installing OpenSSH......Page 122 Insecure r-command Authentication......Page 123 Secure SSH Authentication......Page 125 Implementing SSH to Secure Data......Page 127 Distributing the Public Key......Page 130 The SSH Client......Page 134 SSH Extended Options......Page 136 Understanding Network Encryption......Page 140 Implementing SSH to Secure Data......Page 141 The SSH Client......Page 142 Frequently Asked Questions......Page 143 The SSH Server Basics......Page 145 The Components That Make Up the SSH Server......Page 146 Protocols in Use......Page 147 SSH Authentication Protocol......Page 149 SSH Transport Layer Protocol......Page 151 Connection Protocol......Page 153 Randomness of Cryptography......Page 154 X11 Forwarding......Page 156 Pipes......Page 157 PPP over SSH......Page 158 Reflection for Secure IT Protocol......Page 159 Reflection for Secure IT Authentication......Page 160 Reflection for Secure IT Logging......Page 161 OpenSSH......Page 162 SSH1 e SSH2......Page 163 Dropbear SSH Server and Client......Page 164 WAN – LAN Connections......Page 165 Authentications......Page 166 Server Options......Page 167 Running the Server......Page 171 Basic Server Configuration......Page 173 Authentication......Page 174 Which Communication Is Protected with SSH......Page 177 Running the Server......Page 178 Authentication......Page 179 Frequently Asked Questions......Page 180 SSH on Windows......Page 181 SSH Tectia......Page 182 PuTTY......Page 184 WinSCP......Page 186 Windows and POSIX......Page 188 Interix, SFU, and SUA......Page 189 Win32......Page 190 Windows 2000, Windows XP, or Windows Server 2003......Page 192 Windows Server 2003 R2, Windows Vista (Enterprise or Ultimate), or Windows Server 2008......Page 193 Installing the SUA SDK and Utilities......Page 194 Installing the Software......Page 195 Installing Cygwin and OpenSSH......Page 196 COPSSH......Page 198 SSH Tectia......Page 199 freeSSHd......Page 200 Using Native Windows SSH Servers......Page 203 Frequently Asked Questions......Page 204 Linux SSH......Page 205 Installing OpenSSH Using a Package Manager......Page 206 Controlling Your SSH server......Page 208 Using the Start and Stop Commands......Page 209 Configuring SSH to Ease Your Paranoia......Page 210 Changing the Default Listening Port......Page 211 Allowing and Denying Connections Using hosts Files......Page 212 Binding to a Specific Address......Page 213 Logging into Remote Systems Securely......Page 214 File Transfer Using SSH......Page 215 Executing Secure Commands Remotely......Page 216 Connecting to Your SSH Server from Windows......Page 217 Additional Avenues of Approach......Page 218 Controlling Your SSH Server......Page 219 Additional Avenues of Approach......Page 220 Note......Page 221 Mac SSH......Page 222 Using SSH on a Mac......Page 223 Transferring Files Securely with SCP and SFTP......Page 224 Configuring Your Mac for Remote Access......Page 226 X11 Forwarding......Page 227 Establishing an X11 Forwarding Session with a Remote Computer......Page 228 X11 Forwarding from a Mac to a Remote X Server......Page 229 Simplifying Key Management with the SSH Agent......Page 230 Scripting Securely with SSH......Page 232 Searching for Documents with the Word fish or the Word Chips......Page 233 Managing Local Disks......Page 234 Verifying Permissions......Page 235 Printing Mac OS X Version Information......Page 236 Having Fun with Multimedia......Page 237 Spooking Your In-Laws......Page 238 Scripting Securely with SSH......Page 240 Frequently Asked Questions......Page 241 SSH Command Line and Advanced Client Use......Page 243 Client Configuration......Page 244 Verbose Medium......Page 254 Secure Copy......Page 259 PuTTY Pageant Key Management Utility......Page 260 PuTTY psftp Secure FTP Utility......Page 261 PuTTY pscp Secure Copy Utility......Page 264 Verbose Medium......Page 267 Secure Copy......Page 268 Frequently Asked Questions......Page 269 SSH Server Advanced Use......Page 270 Controlling Access Using ACLs......Page 271 Configuring the Windows Firewall......Page 272 Configuring the Linux Firewall......Page 273 Using TCP Wrappers......Page 274 Using sshd_config Options......Page 275 Using Host Keys for Authentication......Page 276 Maintaining System Time......Page 278 Configuring the Warning Banner......Page 279 Securing User Home Directories......Page 280 Controlling Session Timeouts......Page 281 Logging Using sshd......Page 282 Logging Using Netfilter......Page 283 Security Considerations of Logging......Page 284 Debugging SSH......Page 285 Maintaining System Time......Page 287 Logging Options......Page 288 Debugging SSH......Page 289 Frequently Asked Questions......Page 290 SSH Port Forwarding......Page 292 SSH Port Forwarding Commands......Page 293 Securing E-mail with SSH Local –L Port Forwarding......Page 295 Bypassing Firewalls with SSH Remote –R Port Forwarding......Page 299 Using SSH SOCKS Proxy –D To Tunnel Your HTTP/DNS Traffic......Page 302 Bypassing Firewalls with SSH Remote –R Port Forwarding......Page 307 Using SSH SOCKS Proxy –D to Tunnel Your HTTP/DNS Traffic......Page 308 Frequently Asked Questions......Page 309 C......Page 310 L......Page 311 O......Page 312 S......Page 313 V......Page 316 W......Page 317 New security risks, continuously evolving regulation and increasing security standards have created new and growing needs for secure internal information transfers, which SSH provides. This book addresses these new trends in depth, offering the most up-to-date information on the integration of SSH into a security environment. It covers the newest features and applications of SSH-2 (which received Proposed Standard status from the IETF in 2006). SSH2 is more secure than previous versions and has many expanded uses on a wider variety of computing platforms. Another particular note driving new SSH2 adoption are the requirements of recent legislation (PCI/HIPAA/SOX/FISMA). SSH 2 has become an even more valuable tool, as it provides communications security compliance with the latest standards.

This book offers the most up-to-date information on SSH2 in a practical, hands-on, tutorial-style reference that goes well beyond UNIX implementation. It concentrates on the latest version of SSH 2 with all new information.


* Discover why SSH2 offers more robust security than SSH1 and how to incorporate it into your network administration software toolbox. The most up-to-date information on the next generation of SSH2 and how to incorporate it into your organization's security environment New security risks, continuously evolving regulation and increasing security standards have created new and growing needs for secure internal information transfers, which SSH provides. This book addresses these new trends in depth, offering the most up-to-date information on the integration of SSH into a security environment. It covers the newest features and applications of SSH-2 (which received Proposed Standard status from the IETF in 2006). SSH2 is more secure than previous versions and has many expanded uses on a wider variety of computing platforms. Another particular note driving new SSH2 adoption are the requirements of recent legislation (PCI/HIPAA/SOX/FISMA). SSH 2 has become an even more valuable tool, as it provides communications security compliance with the latest standards. This book offers the most up-to-date information on SSH2 in a practical, hands-on, tutorial-style reference that goes well beyond UNIX implementation. It concentrates on the latest version of SSH 2 with all new information. New security risks, continuously evolving regulation and increasing security standards have created new and growing needs for secure internal information transfers, which SSH provides. This book addresses these new trends in depth, offering the most up-to-date information on the integration of SSH into a security environment. It covers the newest features and applications of SSH-2 (which received Proposed Standard status from the IETF in 2006). SSH2 is more secure than previous versions and has many expanded uses on a wider variety of computing platforms. Another particular note driving new SSH2 adoption are the requirements of recent legislation (PCI/HIPAA/SOX/FISMA). SSH 2 has become an even more valuable tool, as it provides communications security compliance with the latest standards. This book offers the most up-to-date information on SSH2 in a practical, hands-on, tutorial-style reference that goes well beyond UNIX implementation. It concentrates on the latest version of SSH 2 with all new information. * Discover why SSH2 offers more robust security than SSH1 and how to incorporate it into your network administration software toolbox "As networks become more vulnerable to attacks and data leakage, system administrators must protect sessions. SSH is the answer. SSH employs strong industry recognized encryption methods to protect your data from exposure. It makes no difference if you are using SSH across your local area network or the Internet from a remote location; your data will be secured in these encrypted channels. This software replaces telnet and rlogin as your connectivity method and offers protection to your data."--Jacket

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