Paranoid Penguin - Linux VPN Technologies

Which virtual private network is right for you? Mick runs down the options and comes up with some winners and some warnings.

It's tempting to think of OpenSSH purely as a remote shell tool. But the SSH protocol supports the secure tunneling of any single-TCP-port service, not only shells, by using the -L and -R options.

For example, suppose I have a secure shell server in a firewalled but publicly accessible DMZ network and a Microsoft SQL server in my internal network. If I create a firewall rule allowing MS-SQL transactions from the SSH server to the MS-SQL server and if my SSH server allows port forwarding, I could create an SSH tunnel between some remote host and my SSH server that allows remote database clients to send queries to the remote host that are tunneled to the SSH server and forwarded to the MS-SQL server. The SSH command on my remote host would look like this:

bash-#> ssh -L

where is the name or IP address of the MS-SQL server, and is the name or IP address of the DMZed SSH server.

It's even possible to tunnel PPP over SSH, which technically achieves the same thing as IPSec—that is, the ability to tunnel all traffic between two networks. However, this is one of the least efficient means of doing so; it involves much more administrative overhead than the other tools and methods described in this article.

In summary, OpenSSH is a good tool for tunneling traffic from specific applications running on specific hosts; it can be used in this way in both remote-access and point-to-point VPN scenarios. It is less useful, however, for tunneling all traffic between remote networks or users.

See the ssh(1) and sshd_config(5) man pages for more information on using OpenSSH for port forwarding.


Conceptually, Stunnel, an SSL wrapper, provides functionality equivalent to SSH port forwarding. Stunnel is a standard package on most Linux distributions nowadays.

The main difference between Stunnel and SSH is that Stunnel is much more limited; all it does is encrypted port forwarding. Also, because Stunnel really is a sort of front end for OpenSSL, Stunnel requires you to configure and install digital certificates, which perhaps offsets some of its simplicity. Otherwise, Stunnel shares OpenSSH's limitations as a VPN tool.

See the stunnel(8) man page, the Stunnel Web site and my article “Rehabilitating Cleartext Network Applications with Stunnel” (LJ, September 2004) for information on configuring and using Stunnel.


OpenVPN is an SSL/TLS-based user-space VPN tool that encapsulates all traffic between VPN endpoints inside ordinary UDP or TCP packets (ordinary in the sense that they don't require any modifications to your kernel's IP stack). OpenVPN was created because in the opinion of its author, James Yonan, the world needed a less complex alternative to IPSec.

Because no special kernel modules or modifications are necessary, OpenVPN runs purely in user space, making it much easier to port across operating systems than IPSec implementations. And, by virtue of using the standard OpenSSL libraries, OpenVPN, like Stunnel, does a minimum of wheel re-invention. Unlike homegrown cryptosystems, such as those used in the CIPE and tinc VPN packages (see below), all of OpenVPN's critical operations are handled by OpenSSL. OpenSSL itself certainly isn't flawless, but it's under constant scrutiny for security flaws and is maintained by some of the Open Source community's finest crypto programmers.

OpenVPN is a good match for point-to-point VPNs, but until version 2.0 (still in beta as of this writing, November 2004), OpenVPN had the limitation of being able to accommodate only a single tunnel on a given listening port. If you wanted to use OpenVPN to provide remote-access VPN tunnels to ten different users, you needed to run ten different OpenVPN listeners, each using its own UDP port, such as UDP 10201, UDP 10202 and UDP 10203 and seven more. Therefore, if you want to use OpenVPN for remote-access VPNs, you'll be much happier with OpenVPN 2.0 (even in its beta state), unless you have only a handful of users.

OpenVPN is included with SuSE Linux 9.1 and probably other distributions as well. See the OpenVPN Web site for configuration information and for the latest OpenVPN software.

PoPToP and the Linux PPTP Client

IPSec isn't the only low-level VPN protocol used on the Internet. Microsoft's Point-to-Point Tunneling Protocol (PPTP) also has its adherents, mainly because it has been a standard component of Microsoft's server operating systems since Windows NT 4.0 and because, unlike IPSec, which can only tunnel IP packets, PPTP can be used to tunnel not only IP but also other protocols, such as NETBEUI and IPX/SPX.

Linux support for PPTP comes in two flavors, PoPToP on the server side and Linux PPTP Client on the client side.

As handy as it is to tunnel non-IP protocols and as ubiquitous as Windows servers are, PPTP has one big problem. When Bruce Schneier and Dr Mudge analyzed the Windows NT 4.0 implementation of PPTP in 1998, they found serious security flaws that were only partially mitigated by the release of MSCHAPv2 shortly afterward. MSCHAP is an authentication protocol PPTP depends on; it was the source of the worst vulnerabilities Schneier and Mudge found. Schneier has a Web page devoted to their analysis (see Resources).

Schneier and Mudge analyzed Windows NT 4.0; what about a Linux PoPToP server? According to the PoPToP Web site (in “PoPToP Questions and Answers”): “PoPToP suffers the same security vulnerabilities as the NT sever (this is because it operates with Windows clients).”

I do not recommend using PPTP unless you can configure your PPTP server and all PPTP clients to use MSCHAPv2 (not all Windows versions support MSCHAPv2) and you're trying to do something that simply can't be done with IPSec. IPSec is much better designed and is provably more secure. Furthermore, non-IP network protocols aren't as important as they once were; both Windows and Novell Netware can do everything over IP.

I'll stop short of saying something like “you can't use PPTP, because it's lame.” As I argued last month, security is about risk management, not about seeking some sort of utopian state of pure security. After you read up on the Schneier and Mudge controversy, Microsoft's response and MSCHAPv2, and after you carefully examine your particular organization's needs and capabilities, you conceivably could decide that for you, PPTP represents a justifiable compromise between security and functionality—just don't tell anyone I said you should use it!



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If you love blogging then I

spascho's picture

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It's Openswan, not OpenS/WAN

Jacco de Leeuw's picture

It's Openswan, not OpenS/WAN. Says Michael Richardson, a member of the Openswan team.

It's also not IPSec but IPsec, according to RFC 2401.

Another option for those who wish to support Windows and Mac VPN clients is L2TP/IPsec. For end-users it is almost as easy to use as PPTP but much more secure because it is based on IPsec.

Opensource SSL-VPN

wayne's picture

Hey, there is an opensource SSL-VPN. Check this


what about IPSEC and racoon/k

Anonymous's picture

what about IPSEC and racoon/kame?