Search icon CANCEL
Subscription
0
Cart icon
Your Cart (0 item)
Close icon
You have no products in your basket yet
Arrow left icon
Explore Products
Best Sellers
New Releases
Books
Videos
Audiobooks
Learning Hub
Free Learning
Arrow right icon
Mastering OpenVPN
Mastering OpenVPN

Mastering OpenVPN: Master building and integrating secure private networks using OpenVPN

Arrow left icon
Profile Icon Jan Just Keijser Profile Icon Eric F Crist
Arrow right icon
€18.99 per month
Full star icon Full star icon Full star icon Full star icon Half star icon 4.5 (8 Ratings)
Paperback Aug 2015 364 pages 1st Edition
eBook
€22.99 €32.99
Paperback
€41.99
Subscription
Free Trial
Renews at €18.99p/m
Arrow left icon
Profile Icon Jan Just Keijser Profile Icon Eric F Crist
Arrow right icon
€18.99 per month
Full star icon Full star icon Full star icon Full star icon Half star icon 4.5 (8 Ratings)
Paperback Aug 2015 364 pages 1st Edition
eBook
€22.99 €32.99
Paperback
€41.99
Subscription
Free Trial
Renews at €18.99p/m
eBook
€22.99 €32.99
Paperback
€41.99
Subscription
Free Trial
Renews at €18.99p/m

What do you get with a Packt Subscription?

Free for first 7 days. $19.99 p/m after that. Cancel any time!
Product feature icon Unlimited ad-free access to the largest independent learning library in tech. Access this title and thousands more!
Product feature icon 50+ new titles added per month, including many first-to-market concepts and exclusive early access to books as they are being written.
Product feature icon Innovative learning tools, including AI book assistants, code context explainers, and text-to-speech.
Product feature icon Thousands of reference materials covering every tech concept you need to stay up to date.
Subscribe now
View plans & pricing
Table of content icon View table of contents Preview book icon Preview Book

Mastering OpenVPN

Chapter 2. Point-to-point Mode

At first, point-to-point mode using pre-shared keys was the only available option when using OpenVPN. Nowadays, there are multiple ways to use OpenVPN, but point-to-point mode still has its uses. The term point-to-point mode using pre-shared keys is often abbreviated to pre-shared keys.

In point-to-point mode, OpenVPN is configured using pre-shared secret keys for predefined endpoints, and only a single endpoint can connect to a server instance at a time. The term server can be considered misleading, as both endpoints are more or less equal when it comes to functionality. The endpoint that initiates the connection is considered the client, the other endpoint is considered as the server.

We will start off with a demonstration of a very basic example. After that, we will discuss more features that OpenVPN provides. We will look at the following topics:

  • TCP protocol and different ports
  • TAP mode
  • OpenVPN secret keys
  • Routing
  • Complete setup, including IPv6
  • An...

Pros and cons of the key mode

The main use case for using pre-shared key mode is to connect two remote networks, for example, a main office and a remote office of a small company. As soon as more than three users or endpoints are required, it is far easier to use client/server mode, as described in Chapter 4, Client/Server Mode with tun Devices. An example of how to connect three sites together using pre-shared keys is given later in this chapter, and it will become clear why pre-shared key mode does not scale well beyond three sites or users.

The main advantages of using pre-shared key mode are as follows:

  • It is very easy to set up
  • There is no need for public key infrastructure (PKI) or X.509 certificates
  • Can run on limited hardware, such as Linux-based switches or routers

The disadvantages of using pre-shared key mode are:

  • As the name point-to-point indicates, only two endpoints can be used by a single connection. Therefore, this mode does not scale well.
  • Some GUI wrappers for OpenVPN (for...

TCP protocol and different ports

The default protocol that OpenVPN uses is UDP, as it is generally more suitable for VPN connections. However, if the TCP protocol is required, then the preceding example needs to be modified only slightly:

On the listening end, start the OpenVPN server instance:

[root@server] # openvpn \
    --ifconfig 10.200.0.1 10.200.0.2 \
    --dev tun \
    --proto tcp-server

On the client side, the code is as follows:

[root@client] # openvpn \
    --ifconfig 10.200.0.2 10.200.0.1 \
     --dev tun \
    --proto tcp-client \
    --remote openvpnserver.example.com

OpenVPN will now connect over TCP port 1194. It is also possible to override the port number using the --port parameter, for example, --port 5000.

The TAP mode

If non-TCP/IP traffic needs to be passed over the VPN tunnel (for example, legacy AppleTalk or IPX traffic), then a tap device is required. The tap device provides an interface to pass full Ethernet frames over the VPN tunnel. The overhead when passing full...

OpenVPN secret keys

To secure the OpenVPN connection, a secret key is needed. First, we will generate such a key. Then, it needs to be copied to the remote endpoint using a secure channel (example SCP:

$ openvpn --genkey --secret secret.key

Note that it is not necessary to run this command as root (hence the prompt $). The resulting secret key file has the following format:

#
# 2048 bit OpenVPN static key
#
-----BEGIN OpenVPN Static key V1-----
1393ae687606c1f7d465d70227bf63e8
8963e9d1401450002d073d6eab1bffde
b06d1a33cc5c45d4a667016339e921d3
3ac36b1a949eb52e9217e41e4b035a7b
987ddfa9d6766d3b5e4c952dc27f518d
12ccff6b2f0966284382ddc0f62b824a
f576f0982beec9d6a4728d0788499a75
0fd7055ef681404fd463d9862d3a40a9
31fca7d87997c70c07b8303a1b85f1ff
76aa7790e7c341353d2b4ea5049b11a2
51346e7dd39fc1f1e53ae57c46cf60c8
24db00a871262fee78050a9df6a57322
0bb0d980b6cf1be90a2f304f99fb9cde
7cdf72d20e7dee555c7c99950aa4d8e6
86a020c3a63125fb99d56181ff4ca20c
d6711eab15a4d6faf706f2601eb6 61b7
-----END OpenVPN Static key...

Routing

As stated before, the main use case for point-to-point style networks is to connect two remote networks over a secure tunnel. In the previous example, the secure tunnel was established, but no network routes were added.

For the next example, consider the following network layout:

Routing

The client-side network 192.168.4.0/24 (with netmask 255.255.255.0) needs to be routed over the VPN tunnel to the server.

On the listening end (server), we start:

[root@server] # openvpn \
    --ifconfig 10.200.0.1 10.200.0.2 \
    --dev tun \
    --secret secret.key 0\
    --route 192.168.4.0 255.255.255.0 \
    --daemon --log /var/log/movpn-02-server.log

On the client side, the code is as follows:

[root@client] # openvpn \
    --ifconfig 10.200.0.2 10.200.0.1 \
    --dev tun \
    --secret secret.key 1\
    --remote openvpnserver.example.com \
    --daemon --log /var/log/movpn-02-client.log

On the server side, a route statement was added to tell OpenVPN that the network 192.168.4.0/24 is found at the other...

The complete setup

Based on the previous examples, we can now construct a complete production-level setup using configuration files, including routing, logging, IPv6 support, as well as a few other production features that OpenVPN offers.

Consider the following network layout:

The complete setup

For the server, we create the following configuration file movpn-02-02-server.conf:

dev tun
proto udp
local  openvpnserver.example.com
lport  1234
remote openvpnclient.example.com
rport  4321

secret secret.key 0
ifconfig 10.200.0.1 10.200.0.2
route 192.168.4.0 255.255.255.0

tun-ipv6
ifconfig-ipv6 2001:610:120::200:0:1 2001:610:120::200:0:2

user  nobody
groupnobody  # use 'group nogroup' on Debian/Ubuntu
persist-tun
persist-key
keepalive 10 60
ping-timer-rem

verb 3
daemon
log-append /var/log/openvpn.log

For the client, we create the file movpn-02-02-client.conf:

dev tun
proto udp
local  openvpnclient.example.com
lport  4321
remote openvpnserver.example.com
rport  1234

secret secret.key 1
ifconfig 10.200.0...

Pros and cons of the key mode


The main use case for using pre-shared key mode is to connect two remote networks, for example, a main office and a remote office of a small company. As soon as more than three users or endpoints are required, it is far easier to use client/server mode, as described in Chapter 4, Client/Server Mode with tun Devices. An example of how to connect three sites together using pre-shared keys is given later in this chapter, and it will become clear why pre-shared key mode does not scale well beyond three sites or users.

The main advantages of using pre-shared key mode are as follows:

  • It is very easy to set up

  • There is no need for public key infrastructure (PKI) or X.509 certificates

  • Can run on limited hardware, such as Linux-based switches or routers

The disadvantages of using pre-shared key mode are:

  • As the name point-to-point indicates, only two endpoints can be used by a single connection. Therefore, this mode does not scale well.

  • Some GUI wrappers for OpenVPN (for example...

TCP protocol and different ports


The default protocol that OpenVPN uses is UDP, as it is generally more suitable for VPN connections. However, if the TCP protocol is required, then the preceding example needs to be modified only slightly:

On the listening end, start the OpenVPN server instance:

[root@server] # openvpn \
    --ifconfig 10.200.0.1 10.200.0.2 \
    --dev tun \
    --proto tcp-server

On the client side, the code is as follows:

[root@client] # openvpn \
    --ifconfig 10.200.0.2 10.200.0.1 \
     --dev tun \
    --proto tcp-client \
    --remote openvpnserver.example.com

OpenVPN will now connect over TCP port 1194. It is also possible to override the port number using the --port parameter, for example, --port 5000.

The TAP mode

If non-TCP/IP traffic needs to be passed over the VPN tunnel (for example, legacy AppleTalk or IPX traffic), then a tap device is required. The tap device provides an interface to pass full Ethernet frames over the VPN tunnel. The overhead when passing full...

OpenVPN secret keys


To secure the OpenVPN connection, a secret key is needed. First, we will generate such a key. Then, it needs to be copied to the remote endpoint using a secure channel (example SCP:

$ openvpn --genkey --secret secret.key

Note that it is not necessary to run this command as root (hence the prompt $). The resulting secret key file has the following format:

#
# 2048 bit OpenVPN static key
#
-----BEGIN OpenVPN Static key V1-----
1393ae687606c1f7d465d70227bf63e8
8963e9d1401450002d073d6eab1bffde
b06d1a33cc5c45d4a667016339e921d3
3ac36b1a949eb52e9217e41e4b035a7b
987ddfa9d6766d3b5e4c952dc27f518d
12ccff6b2f0966284382ddc0f62b824a
f576f0982beec9d6a4728d0788499a75
0fd7055ef681404fd463d9862d3a40a9
31fca7d87997c70c07b8303a1b85f1ff
76aa7790e7c341353d2b4ea5049b11a2
51346e7dd39fc1f1e53ae57c46cf60c8
24db00a871262fee78050a9df6a57322
0bb0d980b6cf1be90a2f304f99fb9cde
7cdf72d20e7dee555c7c99950aa4d8e6
86a020c3a63125fb99d56181ff4ca20c
d6711eab15a4d6faf706f2601eb6 61b7
-----END OpenVPN Static...

Routing


As stated before, the main use case for point-to-point style networks is to connect two remote networks over a secure tunnel. In the previous example, the secure tunnel was established, but no network routes were added.

For the next example, consider the following network layout:

The client-side network 192.168.4.0/24 (with netmask 255.255.255.0) needs to be routed over the VPN tunnel to the server.

On the listening end (server), we start:

[root@server] # openvpn \
    --ifconfig 10.200.0.1 10.200.0.2 \
    --dev tun \
    --secret secret.key 0\
    --route 192.168.4.0 255.255.255.0 \
    --daemon --log /var/log/movpn-02-server.log

On the client side, the code is as follows:

[root@client] # openvpn \
    --ifconfig 10.200.0.2 10.200.0.1 \
    --dev tun \
    --secret secret.key 1\
    --remote openvpnserver.example.com \
    --daemon --log /var/log/movpn-02-client.log

On the server side, a route statement was added to tell OpenVPN that the network 192.168.4.0/24 is found at the other...

Left arrow icon Right arrow icon
Download code icon Download Code

Description

Security on the internet is increasingly vital to both businesses and individuals. Encrypting network traffic using Virtual Private Networks is one method to enhance security. The internet, corporate, and “free internet” networks grow more hostile every day. OpenVPN, the most widely used open source VPN package, allows you to create a secure network across these systems, keeping your private data secure. The main advantage of using OpenVPN is its portability, which allows it to be embedded into several systems. This book is an advanced guide that will help you build secure Virtual Private Networks using OpenVPN. You will begin your journey with an exploration of OpenVPN, while discussing its modes of operation, its clients, its secret keys, and their format types. You will explore PKI: its setting up and working, PAM authentication, and MTU troubleshooting. Next, client-server mode is discussed, the most commonly used deployment model, and you will learn about the two modes of operation using "tun" and "tap" devices. The book then progresses to more advanced concepts, such as deployment scenarios in tun devices which will include integration with back-end authentication, and securing your OpenVPN server using iptables, scripting, plugins, and using OpenVPN on mobile devices and networks. Finally, you will discover the strengths and weaknesses of the current OpenVPN implementation, understand the future directions of OpenVPN, and delve into the troubleshooting techniques for OpenVPN. By the end of the book, you will be able to build secure private networks across the internet and hostile networks with confidence.

Who is this book for?

If you are familiar with TCP/IP networking and general system administration, then this book is ideal for you. Some knowledge and understanding of core elements and applications related to Virtual Private Networking is assumed.

What you will learn

  • Identify different VPN protocols (IPSec, PPTP, OpenVPN)
  • Build your own PKI and manage certificates
  • Deploy your VPN on various devices like PCs, mobile phones, tablets, and more
  • Differentiate between the routed and bridged network
  • Enhance your VPN with monitoring and logging
  • Authenticate against thirdparty databases like LDAP or the Unix password file
  • Troubleshoot an OpenVPN setup that is not performing correctly

Product Details

Country selected
Publication date, Length, Edition, Language, ISBN-13
Publication date : Aug 28, 2015
Length: 364 pages
Edition : 1st
Language : English
ISBN-13 : 9781783553136
Concepts :
Tools :

What do you get with a Packt Subscription?

Free for first 7 days. $19.99 p/m after that. Cancel any time!
Product feature icon Unlimited ad-free access to the largest independent learning library in tech. Access this title and thousands more!
Product feature icon 50+ new titles added per month, including many first-to-market concepts and exclusive early access to books as they are being written.
Product feature icon Innovative learning tools, including AI book assistants, code context explainers, and text-to-speech.
Product feature icon Thousands of reference materials covering every tech concept you need to stay up to date.
Subscribe now
View plans & pricing

Product Details

Publication date : Aug 28, 2015
Length: 364 pages
Edition : 1st
Language : English
ISBN-13 : 9781783553136
Concepts :
Tools :

Packt Subscriptions

See our plans and pricing
Modal Close icon
€18.99 billed monthly
Feature tick icon Unlimited access to Packt's library of 7,000+ practical books and videos
Feature tick icon Constantly refreshed with 50+ new titles a month
Feature tick icon Exclusive Early access to books as they're written
Feature tick icon Solve problems while you work with advanced search and reference features
Feature tick icon Offline reading on the mobile app
Feature tick icon Simple pricing, no contract
€189.99 billed annually
Feature tick icon Unlimited access to Packt's library of 7,000+ practical books and videos
Feature tick icon Constantly refreshed with 50+ new titles a month
Feature tick icon Exclusive Early access to books as they're written
Feature tick icon Solve problems while you work with advanced search and reference features
Feature tick icon Offline reading on the mobile app
Feature tick icon Choose a DRM-free eBook or Video every month to keep
Feature tick icon PLUS own as many other DRM-free eBooks or Videos as you like for just €5 each
Feature tick icon Exclusive print discounts
€264.99 billed in 18 months
Feature tick icon Unlimited access to Packt's library of 7,000+ practical books and videos
Feature tick icon Constantly refreshed with 50+ new titles a month
Feature tick icon Exclusive Early access to books as they're written
Feature tick icon Solve problems while you work with advanced search and reference features
Feature tick icon Offline reading on the mobile app
Feature tick icon Choose a DRM-free eBook or Video every month to keep
Feature tick icon PLUS own as many other DRM-free eBooks or Videos as you like for just €5 each
Feature tick icon Exclusive print discounts

Frequently bought together


Stars icon
Total 113.97
Troubleshooting OpenVPN
€29.99
Mastering OpenVPN
€41.99
OpenVPN Cookbook
€41.99
Total 113.97 Stars icon
Banner background image

Table of Contents

11 Chapters
1. Introduction to OpenVPN Chevron down icon Chevron up icon
2. Point-to-point Mode Chevron down icon Chevron up icon
3. PKIs and Certificates Chevron down icon Chevron up icon
4. Client/Server Mode with tun Devices Chevron down icon Chevron up icon
5. Advanced Deployment Scenarios in tun Mode Chevron down icon Chevron up icon
6. Client/Server Mode with tap Devices Chevron down icon Chevron up icon
7. Scripting and Plugins Chevron down icon Chevron up icon
8. Using OpenVPN on Mobile Devices and Home Routers Chevron down icon Chevron up icon
9. Troubleshooting and Tuning Chevron down icon Chevron up icon
10. Future Directions Chevron down icon Chevron up icon
Index Chevron down icon Chevron up icon

Customer reviews

Top Reviews
Rating distribution
Full star icon Full star icon Full star icon Full star icon Half star icon 4.5
(8 Ratings)
5 star 62.5%
4 star 25%
3 star 12.5%
2 star 0%
1 star 0%
Filter icon Filter
Top Reviews

Filter reviews by




Hugo Nov 16, 2015
Full star icon Full star icon Full star icon Full star icon Full star icon 5
VPN is an exciting topic for me, but I've had difficult to use it, I was searching for this but some information that I've found aren't for beginners, or are just bad resources, this book explain since the basic concepts, throughout the differences between VPN's, the new features and we know that when we deal with security we have to use the most updated resource, this book gives me a handfull knowledge about OpenVPN, I am not a professional yet, but all the things this book show makes me understand and feel confortable about its configurations, I know that real life projects must be more problematic, but I enjoyed every chapter, I don't had used BSD in the past so I just tried on my Linux and Windows house machines network, I liked the usage in mobile devices and home routers since this is my actual needs, and the part of the log files, even following the book I've missed few details during the configuration, and this log files are hard to me before.
Amazon Verified review Amazon
flying_phoenix Sep 19, 2015
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Love reading the book. Learned a lot about configuring OpenVPN
Amazon Verified review Amazon
Totempole Oct 18, 2015
Full star icon Full star icon Full star icon Full star icon Full star icon 5
This is the go-to book for going from learning everything about OpenVPN. Not only that, but it walks you through the basics, it tells you what a VPN is, the types of VPNs, their pros and cons. This is the book for everyone looking into mastering OpenVPN, from the home user (setting it up in your own router, and using your mobile devices as clients) to the network admin (client/server setup).
Amazon Verified review Amazon
Matteo Guglielmi Oct 10, 2015
Full star icon Full star icon Full star icon Full star icon Full star icon 5
Finally a comprehensive and up-to-date book (Aug. 2015) on OpenVPN. The concepts and available options behind the implementation of virtual private networks using OpenVPN are well explained and worked out with several examples. The book is complete and self-contained. No previous knowledge on OpenVPN is required. Personally, I found Chapter 7 (Scripting and Plugins) extremely helpful: understanding the exact order in which all different scripts are executed is what helped me the most with the implementation of (powerful!) vpn solutions. The book has few typos in some of the worked out examples but they can easily be spotted out.
Amazon Verified review Amazon
Carles Oct 14, 2015
Full star icon Full star icon Full star icon Full star icon Full star icon 5
This book is targeted to system administrators willing to deploy an extra layer of security for his users or customers which need to access private infraestructures from the internet using OpenVPN software. This book it's written in plain language and goes straight to the point but a good knowledge on networking is advised to get the most out of the book. The book can be used as a complete guide to deploy the service from the ground or to strengthen security or fine tune already existing VPN scenarios. The book also gives recommendations on how to scale in the future and be aware of possible weaknesses of the system. In overall it's a very good source of information on this matter and I recommend it without any doubt.
Amazon Verified review Amazon
Get free access to Packt library with over 7500+ books and video courses for 7 days!
Start Free Trial

FAQs

What is included in a Packt subscription? Chevron down icon Chevron up icon

A subscription provides you with full access to view all Packt and licnesed content online, this includes exclusive access to Early Access titles. Depending on the tier chosen you can also earn credits and discounts to use for owning content

How can I cancel my subscription? Chevron down icon Chevron up icon

To cancel your subscription with us simply go to the account page - found in the top right of the page or at https://subscription.packtpub.com/my-account/subscription - From here you will see the ‘cancel subscription’ button in the grey box with your subscription information in.

What are credits? Chevron down icon Chevron up icon

Credits can be earned from reading 40 section of any title within the payment cycle - a month starting from the day of subscription payment. You also earn a Credit every month if you subscribe to our annual or 18 month plans. Credits can be used to buy books DRM free, the same way that you would pay for a book. Your credits can be found in the subscription homepage - subscription.packtpub.com - clicking on ‘the my’ library dropdown and selecting ‘credits’.

What happens if an Early Access Course is cancelled? Chevron down icon Chevron up icon

Projects are rarely cancelled, but sometimes it's unavoidable. If an Early Access course is cancelled or excessively delayed, you can exchange your purchase for another course. For further details, please contact us here.

Where can I send feedback about an Early Access title? Chevron down icon Chevron up icon

If you have any feedback about the product you're reading, or Early Access in general, then please fill out a contact form here and we'll make sure the feedback gets to the right team. 

Can I download the code files for Early Access titles? Chevron down icon Chevron up icon

We try to ensure that all books in Early Access have code available to use, download, and fork on GitHub. This helps us be more agile in the development of the book, and helps keep the often changing code base of new versions and new technologies as up to date as possible. Unfortunately, however, there will be rare cases when it is not possible for us to have downloadable code samples available until publication.

When we publish the book, the code files will also be available to download from the Packt website.

How accurate is the publication date? Chevron down icon Chevron up icon

The publication date is as accurate as we can be at any point in the project. Unfortunately, delays can happen. Often those delays are out of our control, such as changes to the technology code base or delays in the tech release. We do our best to give you an accurate estimate of the publication date at any given time, and as more chapters are delivered, the more accurate the delivery date will become.

How will I know when new chapters are ready? Chevron down icon Chevron up icon

We'll let you know every time there has been an update to a course that you've bought in Early Access. You'll get an email to let you know there has been a new chapter, or a change to a previous chapter. The new chapters are automatically added to your account, so you can also check back there any time you're ready and download or read them online.

I am a Packt subscriber, do I get Early Access? Chevron down icon Chevron up icon

Yes, all Early Access content is fully available through your subscription. You will need to have a paid for or active trial subscription in order to access all titles.

How is Early Access delivered? Chevron down icon Chevron up icon

Early Access is currently only available as a PDF or through our online reader. As we make changes or add new chapters, the files in your Packt account will be updated so you can download them again or view them online immediately.

How do I buy Early Access content? Chevron down icon Chevron up icon

Early Access is a way of us getting our content to you quicker, but the method of buying the Early Access course is still the same. Just find the course you want to buy, go through the check-out steps, and you’ll get a confirmation email from us with information and a link to the relevant Early Access courses.

What is Early Access? Chevron down icon Chevron up icon

Keeping up to date with the latest technology is difficult; new versions, new frameworks, new techniques. This feature gives you a head-start to our content, as it's being created. With Early Access you'll receive each chapter as it's written, and get regular updates throughout the product's development, as well as the final course as soon as it's ready.We created Early Access as a means of giving you the information you need, as soon as it's available. As we go through the process of developing a course, 99% of it can be ready but we can't publish until that last 1% falls in to place. Early Access helps to unlock the potential of our content early, to help you start your learning when you need it most. You not only get access to every chapter as it's delivered, edited, and updated, but you'll also get the finalized, DRM-free product to download in any format you want when it's published. As a member of Packt, you'll also be eligible for our exclusive offers, including a free course every day, and discounts on new and popular titles.