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Aug 01 MacTech Online

Volume Number: 17 (2001)
Issue Number: 08
Column Tag: MacTech Online


by Jeff Clites


When the Internet was first growing up, it was developing in a rather safe environment. In fact, to the inventors it was probably a miracle that it worked at all. Now, however, those halcyon days are gone, and we live in less innocent times, where security is a genuine concern—it isn’t practical these days to just assume that things will be safe by default. There are a number of steps that users need to take these days to secure their systems, and this month we are going to look at one of them, ssh. It’s a small but important piece.

What’s ssh?

In brief, ssh (the Secure Shell) is a cryptographically secure replacement for telnet. The name is actually a bit of a misnomer—it isn’t really a shell itself, but rather a mechanism for interacting with a remote shell over a secure communication channel. It’s an indispensable tool for working with Mac OS X in a networked environment—like telnet, it allows you to quickly connect to remote machines, which is handy if not essential for a variety of administration and other tasks. In fact, the most significant security enhancement that ssh gives you may not be that it encrypts the contents of your remote session (which it does), but rather that it encrypts the login exchange itself, meaning that your password is never sent unencrypted over the network. Even in a supposedly secure environment, for instance behind a corporate firewall, it’s a good idea to use ssh instead of telnet whenever possible (which basically means whenever the two machines which are communicating both have it installed), both because it adds an extra bit of security, and also because it will get you into the habit of using it and making sure it is installed and available on all machines you routinely connect to, so that when you are operating in a less secure environment (for instance, if you need to connect from off site) you will be in the habit of reaching for ssh and will be opting for security by default.

Mac OS X has ssh installed by default (as part of a regular update package), and you can use it to connect with remote machines without further setup. To enable connections to your machine you merely need to enable remote login in the Sharing pane of System Preferences (after the update which installs ssh on Mac OS X, this setting is connected to ssh rather than to telnet, which is then disabled by default). The ssh “server” component (sshd) can be run out of inetd, but it is more commonly run as a standalone daemon. If you need to install ssh separately (either because you wish to install a newer version or because your current install is damaged), there are instruction on Stepwise for building and installing OpenSSH under Mac OS X. (The article also includes instructions for compiling in support for using tcpwrappers to further secure things by restricting remote login to a specific set of hosts and adding additional logging.) This version of ssh is free and open-source (part of the OpenBSD project, in fact), and leverages the OpenSSL library for many of its cryptographic algorithms. There are commercial versions available as well (and older free version from commercial vendors), but for most users OpenSSH is a good choice. OpenSSH tries very hard to avoid the use of patented algorithms in its implementation, in order to avoid the attendant restrictions to free development and distribution, and consequently does not support some of the algorithms found in commercial versions. This can be seen as either a virtue or a shortcoming, but in practice it does not interfere with its use.

Building OpenSSH 2.9 on Mac OS X 10.0.x

Securing your Host—tcpwrappers

The SHH Suite

Overall, ssh has a great deal of flexibility in the details of its use. It supports a variety of authentication schemes, from RSA or Kerberos-based authentication to simple passwords or automatic login between trusted hosts; you can choose from several different algorithms (also called ciphers) for the encryption; and you can use ssh for port-forwarding to wrap insecure protocols inside of a secure transfer stream. And in addition to enabling remote login sessions, the ssh distribution contains several related tools which take advantage of ssh’s base facilities for secure communication. For file transfer, there is scp (an analog of rcp and ultimately cp, if you are familiar with those), which is used to copy files between systems over an ssh-based, encrypted channel. Server environments today are often set up without ftp installed in order to enhance security, and in such situations scp is the tool of choice for moving files onto and off of these systems. In addition to encryption, scp also supports compression of files during transit in order to speed transfer, using the same algorithm as gzip. (Compression is also supported by ssh itself, but the benefits are more likely to be noticeable during large file transfers than during a standard interactive login session, although over slow connections compression could make ssh “faster” than telnet for interactive use.) The scp tool has the same semantics as cp, so that source and destination are specified when invoking the tool, rather then being chosen interactively as is commonly done with ftp tools. This can be somewhat inconvenient, as you need to know the exact path to use on the remote system before invoking the tool, which will often necessitate a separate ssh login to “browse around” the remote filesystem to determine the correct path. On the plus side, scp can be used to transfer files between remote systems—neither the source nor the destination needs to be local.

On the other hand, if you need the convenience and flexibility of the interactivity of ftp, you might find sftp more to your liking. It’s a newer addition to the ssh family, and is likely to be less widely deployed at this time. It provides an ftp-like interactive session for file transfer, with similar commands to those used by ftp. Technically, sftp is not itself a secure protocol, but rather it is a protocol designed to be used over a secure channel, provided by ssh. There is a separate executable, sftp-server, which is used by OpenSSH to enable sftp on the server side, but it is invoked by the sshd daemon rather than running separately, so it requires minimal configuration and setup to get it running. One caveat is that sftp is reported to be significantly slower than the traditional scp, although it’s not clear whether this is inherent to the protocol it uses, or if it’s just the result of a still-evolving implementation. Note also that sftp is not simply ftp secured via ssh port-forwarding, because ftp’s use of two separate TCP/IP connections for control commands and data transfer makes this difficult to do; instead, sftp uses a single stream to do its work.


Online, you can find most of the essential information you need at the OpenSSH web site, including download locations, online manual pages, and a short FAQ, as well as links to other sites with articles and even more information. There is also another ssh FAQ available online, more general but somewhat geared toward the commercial versions of ssh.


OpenSSH Manual pages


OpenSSH Articles

The Secure Shell Frequently Asked Questions

There are also a couple of books available devoted entirely to ssh. They can provide you with all the details and options you have for setting up and using ssh on your systems, as well as using it for advanced applications such as tcp port forwarding. Possibly more importantly, they’ll guide you through the minefield of terminology surrounding different version of ssh products and protocols (which are very easy to confuse), and spell out differences and interoperability issues surrounding the different implementations. Try either SSH, The Secure Shell: The Definitive Guide (ISBN: 0-596-00011-1) from O’Reilly and Associates, or UNIX Secure Shell (ISBN: 0071349332) from Osborne. There is also an excellent web site to accompany the O’Reilly book, with extensive reference information and links to protocol specifications and other reference material.

SSH, The Secure Shell: The Definitive Guide

For further helpful info, check out the top 10 FAQ list from Richard Silverman, one of the authors of the O’Reilly book. The security-minded user (which should be everyone, right?) will also want to check out a recent article on about a potential security weakness with ssh, as well as the follow-up rebuttal article from Richard Silverman which corrects some factual errors and gives a less alarmist perspective. For further security info, take a look at the OpenSSH Security page.

Top Ten Secure Shell FAQs

The End of SSL and SSH?

dsniff and SSH: Reports of My Demise are Greatly Exaggerated

OpenSSH Security

Finally, for those interested in some of the more advanced features of ssh, start with the SSH Protocol Architecture internet-draft from the IETF for an extensive high-level overview of the protocol. Then, check out an article from the O’Reilly Network on using an ssh tunnel to increase the security of 802.11b wireless networking, such as that used by AirPort.

SSH Protocol Architecture

Using SSH Tunneling

If you are not yet using Mac OS X (and why aren’t you, huh?), then you can still connect via ssh to remote machines using one of the two clients for the Classic Mac OS. There is NiftyTelnet SSH (based on NiftyTelnet itself) supporting the SSH1 protocol, including scp capabilities, and MacSSH, which is a modified version of BetterTelnet supporting SSH2. Both are available free of charge. If you are running Mac OS X but would prefer a graphical file-transfer tool, try RBrowser, a GUI-based ftp tool which also supports ssh- and scp-based file browsing and transfer. It is still in beta testing, and will require a licensing fee once it is final.

NiftyTelnet SSH




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