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Home > Cloud & Networking > Networking > Mastering OpenVPN
Mastering OpenVPN
Mastering OpenVPN

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

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Profile Icon Jan Just Keijser Profile Icon Eric F Crist
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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...

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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 : 9781783553143
Category :
Cloud & Networking
Concepts :
Networking
Tools :
OpenVPN

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Product Details

Publication date : Aug 28, 2015
Length: 364 pages
Edition : 1st
Language : English
ISBN-13 : 9781783553143
Category :
Cloud & Networking
Concepts :
Networking
Tools :
OpenVPN

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Table of Contents

11 Chapters
1. Introduction to OpenVPN Chevron down icon Chevron up icon
1. Introduction to OpenVPN
What is a VPN?
Types of VPNs
Comparison of VPNs
OpenVPN packages
OpenVPN internals
Summary
2. Point-to-point Mode Chevron down icon Chevron up icon
2. Point-to-point Mode
Pros and cons of the key mode
TCP protocol and different ports
OpenVPN secret keys
Routing
The complete setup
Three-way routing
Bridged tap adapter on both ends
Combining point-to-point mode with certificates
Summary
3. PKIs and Certificates Chevron down icon Chevron up icon
3. PKIs and Certificates
An overview of PKI
OpenVPN server certificates
OpenVPN client certificates
Other features
Multiple CAs and CRLs
Extra security – hardware tokens, smart cards, and PKCS#11
Summary
4. Client/Server Mode with tun Devices Chevron down icon Chevron up icon
4. Client/Server Mode with tun Devices
Understanding the client/server mode
Setting up the Public Key Infrastructure
Initial setup of the client/server mode
Adding extra security
Basic production-level configuration files
Routing and server-side routing
Redirecting the default gateway
Client-specific configuration – CCD files
Client-side routing
The OpenVPN status file
The OpenVPN management interface
Session key renegotiation
Using IPv6
Advanced configuration options
Summary
5. Advanced Deployment Scenarios in tun Mode Chevron down icon Chevron up icon
5. Advanced Deployment Scenarios in tun Mode
Enabling file sharing over VPN
Using LDAP as a backend authentication mechanism
Filtering OpenVPN
Windows network locations – public versus private
Using OpenVPN with HTTP or SOCKS proxies
Summary
6. Client/Server Mode with tap Devices Chevron down icon Chevron up icon
6. Client/Server Mode with tap Devices
The basic setup
Enabling client-to-client traffic
Using the tap device (bridging)
Using an external DHCP server
Checking broadcast and non-IP traffic
Comparing tun mode to tap mode
Summary
7. Scripting and Plugins Chevron down icon Chevron up icon
7. Scripting and Plugins
Scripting
Plugins
Summary
8. Using OpenVPN on Mobile Devices and Home Routers Chevron down icon Chevron up icon
8. Using OpenVPN on Mobile Devices and Home Routers
Using the OpenVPN for an Android app
Using the OpenVPN Connect app for Android
Using the OpenVPN Connect app for iOS
Integrating smart phones into an existing VPN setup
Using a home router as a VPN client
Using a home router as a VPN server
Summary
9. Troubleshooting and Tuning Chevron down icon Chevron up icon
9. Troubleshooting and Tuning
How to read the log files
Fixing common configuration mistakes
Troubleshooting routing issues
How to optimize performance by using ping and iperf
Analyzing OpenVPN traffic by using tcpdump
Summary
10. Future Directions Chevron down icon Chevron up icon
10. Future Directions
Current strengths
Current weaknesses
Where we are going
Summary
Index Chevron down icon Chevron up icon
Index

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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
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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

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About the authors

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Profile icon Jan Just Keijser
Jan Just Keijser
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Jan Just Keijser is an open source professional from Utrecht, the Netherlands. He has a wide range of experience in IT, ranging from providing user support, system administration, and systems programming to network programming. He has worked for various IT companies since 1989. He was an active USENET contributor in the early 1990s and has been working mainly on Unix/Linux platforms since 1995. Currently, he is employed as a senior scientific programmer in Amsterdam, the Netherlands, at Nikhef, the institute for subatomic physics from the Dutch Foundation for Fundamental Research on Matter (FOM). He works on multi-core and many-core computing systems and grid computing as well as smartcard applications. His open source interests include all types of virtual private networking, including IPSec, PPTP, and, of course, OpenVPN. In 2004, he discovered OpenVPN and has been using it ever since. His first book was OpenVPN 2 Cookbook by Packt Publishing in 2011, followed by Mastering OpenVPN, also by Packt Publishing, in 2015.
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Profile icon Eric F Crist
Eric F Crist
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Eric F Crist hails from Cottage Grove, Minnesota, and he works as a product and systems engineer for Abbott. He has a relatively wide range of professional and life experience starting from physical security and access control as a low-voltage technician into software development, system administration, and software development. Eric has been a core member of the OpenVPN community since 2008 and helps manage the open source online resources. He also wrote ssl-admin, and he is a lead for Easy-RSA, both of which help manage Certificate Authorities and chains. Eric collaborated with Jan Just Keisjer for the book, Mastering OpenVPN, in 2015, also for Packt.
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