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October 18, 2005

Toolbox: Encrypt Telnet via IPsec in 10 Steps


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As ubiquitous as Telnet is, many security and IT administrators shun it because Telnet traffic passing between the client and server is unencrypted and visible to any network snooper who might be listening. Before you resort to cobbling together a Win32 port of OpenSSH (a freeware version of the Secure Shell—SSH—suite of network-connectivity tools) or spending thousands of dollars for a commercial version of SSH, consider using IPsec to encrypt your Telnet traffic. Together, Telnet and IPsec provide a secure and relatively easy-to-deploy solution for remote-console access for Windows Server 2003 servers. Although configuring IPsec can be complicated, here I provide 10 quick, straightforward steps to follow for encrypting Telnet over IPsec. You can also extend these examples for encrypting other network traffic to suit your own security needs.

A Few Preliminaries
The sample configuration that I'll walk you through uses Kerberos—the Windows IPsec default authentication method—which means that your client and server must reside in the same or trusted domains. IPsec supports alternative authentication mechanisms (e.g., certificates) that you can use if Kerberos isn't an option for your domain. However, such mechanisms can be trickier to set up and require an existing public key infrastructure (PKI). . . .


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