Review of OpenVPN: Building and Integrating Virtual Private Networks by Markus Feilner (Packt Publishing)


This is an edited version of a post that originally appeared on a blog called The Michigan Telephone Blog, which was written by a friend before he decided to stop blogging. It is reposted with his permission. Comments dated before the year 2013 were originally posted to his blog. In order to comply with Federal Trade Commission regulations, I am disclosing that he received a free product sample of the item under review prior to writing the review, and that any links to in this article are affiliate links, and if you make a purchase through one of those links I will receive a small commission on the sale.
Cover of OpenVPN: Building and Integrating Virtual Private Networks
Cover of OpenVPN: Building and Integrating Virtual Private Networks

Before I start, let me give you a brief description of what’s in each chapter (this is taken directly from the Packt Publishing web site):

  • Chapter 1 looks at what VPNs are, how they evolved during the last decade, why it is necessary to modern enterprises, how typical VPNs work. The chapter also covers some essential networking concepts.
  • Chapter 2 explains VPN security issues, including symmetric and asymmetric encryption, the SSL/TLS library, and SSL certificates.
  • Chapter 3 introduces OpenVPN. In this chapter, we learn about the history of OpenVPN, how OpenVPN works, and how OpenVPN compares to IPSec VPN applications.
  • Chapter 4 covers installing OpenVPN on both Windows, the Mac, Linux, and FreeBSD. It covers the installation on Linux from the source code and RPM packages. Installation on Suse and Debian is covered in detail.
  • In Chapter 5, an encryption key for OpenVPN is created and it is then used to setup up our first OpenVPN Tunnel between two windows systems in the same network. The key is then copied on a Linux system and this system is connected through a tunnel to the first windows machine.
  • Chapter 6 shows how to create x509 server and client certificates for use with OpenVPN. easy-rsa which comes with OpenVPN and is available for both Windows and Linux is used.
  • Chapter 7 reviews the syntax of the command line tool openvpn, which enables building tunnels quickly. The configuration options of openvpn are covered in detail with examples.
  • Chapter 8 shows how to make the example tunnels created earlier safer and persistent by choosing a reliable combination of configuration file parameters. It then covers how to configure firewalls on Linux and Windows to work with OpenVPN.
  • Chapter 9 focuses on using xca, the advanced Windows tool with which x509 certificates can be easily managed. Its Linux equivalent, Tinyca2, which can even manage multiple certificate authorities, is also covered.
  • Chapter 10 covers advanced OpenVPN configurations, including Tunneling through a proxy server, pushing routing commands to clients, pushing and setting the default route through a tunnel, Distributed compilation through VPN tunnels with distcc, and OpenVPN scripting.
  • Chapter 11 shows how to debug and monitor VPN tunnels. It covers standard networking tools that can be used for scanning and testing the connectivity of a VPN server.

Although this may seem like a strange subject for this blog, I have recently become interested in the concept of Virtual Private Networks (VPN) because of the increasing number of attacks on Asterisk-based system based on spoof SIP credentials. SIP, the most popular protocol for VoIP, is an inherently insecure protocol – it relies on password protection only, and on most Asterisk boxes and in many VoIP devices and software products, the password is stored in plain text. On many systems, the user name is the same as the extension number, so all a potential intruder has to do is start a brute-force attack guessing passwords. The use of strong passwords along with the use of software like Fail2Ban (with iptables) can help minimize the exposure, but in the end it’s still only password protection.

Therefore, my feeling is that it would be much better to restrict extensions to access from within the local network (wherever possible), using the permit/deny fields in FreePBX or some similar mechanism, and then “tunnel” remote extensions through a secure VPN, so they appear to be on the local network.  The VPN could do the heavy lifting for security (even making the actual calls secure, although that wasn’t a priority in my situation).  My problem was that I knew next to nothing about VPN’s, and most of the pages on the Web seemed to assume at least some prior knowledge.  I needed something that would take me from zero knowledge to VPN guru.  Unfortunately, at my age it’s a case of “the spirit is willing but the brain is a bit weak”, so I realized that the “guru” part might not come very quickly (just as a comparison, I’ve been playing with FreePBX since back in the Asterisk@Home days, and there’s still a lot I don’t understand, but for the first year or so I felt totally lost).

Since the folks at Packt Publishing were willing to send me a review copy of OpenVPN: Building and Integrating Virtual Private Networks, I decided to see if I could actually learn anything from the book.  The first thing you need to know is that there are many types of VPN’s out there, and each will only communicate with its own kind, as it were.  The problem with most other tunnels is that they are either not all that secure, or contain proprietary code, or are incredibly complicated to set up and use (or some combination of the above).  OpenVPN has several advantages, perhaps the biggest being that it’s open source (so you can, if you are so inclined, examine the code and make sure there are no “backdoors” built in), that it can be as secure as you want it to be (and it’s not that difficult to make it very secure), and that it doesn’t rely on a third-party service over which you have no control (like one VPN application that touts itself as “zero-configuration”). So of all the VPN methods out there, OpenVPN seemed like a logical choice.

Now, having said that, the book covers its subject in a very logical manner.  Advanced readers (those already familiar with the principles behind VPNs) might find the introductory material in the first chapters a bit tedious, but believe me, it was just what I needed to help me get a grasp on the subject. As you go further through the book, there are many actual examples, first showing how to set up a working VPN tunnel, then how to add additional security, and finally how to troubleshoot connections.  If you are brand new at this, like me, you will probably find that you learn a great deal from the first chapters but find the latter chapters (especially Chapter 10) a bit beyond your comprehension at first.  However, the person who has some networking or VPN experience under their belt may think the first chapters a bit elementary, but will find the real meat they are looking for in the latter parts of the book. Either way, I guarantee you will come away with a greater comprehension of the subject.

The book shows how to install OpenVPN on several platforms (Windows, Mac OS X using Tunnelblick, FreeBSD, and SuSE, Debian, and Redhat/Fedora based versions of Linux), but it seems like some platforms are better covered than others.  A disproportionate number of examples and screenshots seem to be based on a Windows installation, whereas the Mac gets very little coverage. Because there are so many variations of Linux, the coverage there is mixed, although it seems like SuSE and Debian are better covered than Fedora-based versions, which was just a little bit disappointing because most Asterisk and FreePBX systems are based on CentOS, which is a Fedora-based OS. But most of the information in this book is not OS specific, so I didn’t have any real problem following along.

The biggest disappointment for me was in Chapter 8, where the book covers the use of Webmin, but primarily as an aid to administration of the Shorewall firewall.  Many Asterisk/FreePBX systems don’t use Shorewall, but instead use iptables (if they have a firewall on the Asterisk server at all).  But what was really disappointing was that there was no mention of, nor instructions for the use of the OpenVPN + CA module for Webmin (page is in Italian, but here is a description in English). I can only guess that because the book was first released in May,  2006 and version 1.0 of the Webmin module had only just been released in January of that same year, the author perhaps hadn’t had an opportunity to work with the module before the final draft of the book was submitted to the publisher. I hope that if this book is ever updated and republished, there will be consideration given to adding a chapter on the use of the Webmin module to set up and administer OpenVPN. In the meantime, you can find instructions for using the OpenVPN + CA module in The ‘Point and Click’ Home VPN HowTo Guide.

That said, I felt I learned a great deal from this book.  I was able to set up an OpenVPN server (using the Webmin module, but the book definitely helped me understand the purpose of the various options, and when I checked the configuration file that the module generated I was able to spot a couple of things that weren’t the way they should be for my setup and was able to change them) and the Windows client.  It all worked beautifully.

My project now, when I have absolutely nothing else to do, is trying to get the OpenVPN client running on an Asus WL-520gu router that has the DD-WRT firmware installed (I inherited this project from someone else who couldn’t do it).  So far this has proven to be a tough nut to crack – although it should be easy because (if you get the right version of DD-WRT) there is a built-in OpenVPN client with a handy configuration page, it just doesn’t seem to work “out of the box” – and from what I’m reading on the ‘net, for every one person who says they’ve got it working, there are about twenty others who have become incredibly frustrated by the process (example here – note that the original poster says he got it working, but that’s followed by about 16 pages of comments, mostly by people who just can’t seem to get it to go).  It’s a bit strange because the Windows client will work perfectly (indicating it’s not an issue with the server) but the firmware client in DD-WRT just doesn’t seem to work.  If I ever get it figured out, I’ll try to post what I did in this blog, but so far I’ve had no luck.  That, however, is not the fault of the book – in my opinion it’s the fault of the writers of the DD-WRT firmware, who apparently included a half-baked OpenVPN client interface in the firmware (I know, it’s free software so I can’t really complain, but one does wish that they’d taken a bit more care to make sure it worked).

After having read the book, I do feel fairly confident that if I should throw in the towel and decide to dump DD-WRT and install a different firmware on the router (I’m thinking about trying the Tomato firmware with USB support) I would be able to install an OpenVPN client from scratch and make it work.  Probably the main reason I haven’t wanted to do that is because I very much prefer using a GUI to do things, and would like to try to make the OpenVPN GUI in DD-WRT work (even if it requires a little help), but so far that doesn’t seem to be panning out.

But I digress a bit – anyway, if you are wanting to learn about OpenVPN, whether or not you are a rank beginner you will benefit from this book. The numerous examples and screenshots make it almost impossible to fail to get an OpenVPN tunnel up and running (providing you’re not using a questionable firmware client). And, as I said above, the book is laid out in a very logical progression, so I really didn’t feel totally lost at any point (as so often happens when I try to read technical books). Especially in the case where your boss suddenly decides he needs VPN tunneling capability, and wants you to have one up and running in a very short timeframe, this would be the book to get!

OpenVPN: Building and Integrating Virtual Private Networks by Markus Feilner (Amazon affiliate link)

EDIT: This book has been updated and expanded under a new title — see Mini-review of Beginning OpenVPN 2.0.9 by Markus Feilner and Norbert Graf (Packt Publishing)

2 thoughts on “Review of OpenVPN: Building and Integrating Virtual Private Networks by Markus Feilner (Packt Publishing)

  1. I’ve never found the answers to the following questions.
    What happens with UDP packets in a VPN? If UDP is encapsulated inside a TCP tunnel, if the TCP connection doesn’t succeed and need to resend, would it mean that we are retransmitting UDP packets?
    Wouldn’t point to point encryption of UDP packets be a better option?
    Appreciate any insight.

  2. NOTICE: All comments above this one were imported from the original Michigan Telephone Blog and may or may not be relevant to the edited article above.

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