Troubleshooting OpenVPN

By Eric F Crist

About This Book

• This is the first book on the market that resolves your issues related to troubleshooting OpenVPN
• Ensure your organization's private network is protected 24x7 by resolving OpenVPN issues instantly
• Save time and costs by troubleshooting to reduce the impact on your business

Who This Book Is For

The book is for system administrators who are experienced and well versed with OpenVPN. You should possess intermediate to master level proficiency with OpenVPN. All OpenVPN users can leverage this book.

• Language: English
• Publisher: Packt Publishing
• Release date: Mar 17, 2017
• ISBN: 9781786466938

Eric F Crist

Eric F Crist is an IT professional with experience in hardware and software systems integration. With a few others, he has had a key role in building the OpenVPN community to what it is today. He works in research and development as a principal computer system specialist for St. Jude Medical. His role involves system engineering, configuration management, and cyber security analysis for products related to the Cardiovascular Ablation Technology division. You can find him online at the Freenode and EFNet IRC networks as ecrist. He calls the Twin Cities, Minnesota, his home and lives with his wife, DeeDee, his son, Lance, and his daughter, Taylor.

Book preview

Table of Contents

Troubleshooting OpenVPN

Credits

About the Author

About the Reviewer

www.PacktPub.com

Why subscribe?

Customer Feedback

Preface

What this book covers

What you need for this book

Who this book is for

Conventions

Reader feedback

Customer support

Errata

Piracy

Questions

1. Troubleshooting Basics

A recommended toolkit

Log search and filtering

grep

less, more, and most

Regular expressions

Network sniffing and analysis

tcpdump

traceroute

mtr

ping

Wireshark

X.509 verification and inspection

OpenSSL

Wireshark

Troubleshooting basics

Summary

2. Common Problems

Narrowing the focus

Sample scenarios

Scenario 1--unable to access VPN

Scenario 2--cannot access external web when on VPN

Suspecting recent changes

Supported operating systems

Embedded devices

Semi-embedded systems

Virtual servers

IP addresses

Firewalls

Duplicate client certificates

Overcomplication

Summary

3. Installing OpenVPN

Common installation problems

Compiling OpenVPN

Packages and installers

The advantages of precompiled installers

Driver installation

Alternative clients

Summary

4. The Log File

Logging options

Logging levels

Verbosity 0

Verbosity 1

Verbosity 4

Verbosity 7

Common log messages

Startup messages

Version and compile string

Option warnings

Configuration parameters

Operational messages

Certificate messages

Summary

5. Client and Server Startup

File and process permissions

Privilege de-escalation

Networking privileges

Port assignment and use

Multiple daemons

Adapter and routing table changes

Chroot

Scripting

Up and down scripts

Connect and disconnect scripts

UDP troubleshooting

UDP and firewalls

Summary

6. Certificates and Authentication

File permissions

Pre-shared keys

Certificate authentication

Certificate chain overview

The Certificate Revocation List

System date and time

Authentication and plugins

Usernames and passwords

--ccd-exclusive

Summary

7. Network and Routing

Connectivity

Inbound connection--server

Publicly addressed server

Privately addressed server with port forwarding

Outbound connection--client

Firewall filters and inspection

TLS authentication

Routing

Internal routing

External routing

Pushing routes

Routes behind clients

Kernel versus process routing

Route conflicts

Redirect gateway

General network concerns

Path MTU and MSS

Summary

8. Performance

Networking

Rate limiting

Cryptographic performance

Library differences

Cipher and AES-NI

Result summary

Single thread

Summary

9. External Problems

Inspection and filtering

Obfuscation

Encryption

Geographic and source address exclusions

What can be done

Source IP address

DNS settings

Routing path performance

Summary

Useful links

Manual or man pages

Release notes

Support channels

Troubleshooting OpenVPN

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Troubleshooting OpenVPN

Copyright © 2017 Packt Publishing

All rights reserved. No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, without the prior written permission of the publisher, except in the case of brief quotations embedded in critical articles or reviews.

Every effort has been made in the preparation of this book to ensure the accuracy of the information presented. However, the information contained in this book is sold without warranty, either express or implied. Neither the author, nor Packt Publishing, and its dealers and distributors will be held liable for any damages caused or alleged to be caused directly or indirectly by this book.

Packt Publishing has endeavored to provide trademark information about all of the companies and products mentioned in this book by the appropriate use of capitals. However, Packt Publishing cannot guarantee the accuracy of this information.

First published: March 2017

Production reference: 1150317

Published by Packt Publishing Ltd.

Livery Place

35 Livery Street

Birmingham 

B3 2PB, UK.

ISBN 978-1-78646-196-4

www.packtpub.com

Credits

About the Author

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.

I would like to sincerely thank my wife, DeeDee, for encouraging me to write this book. Without your prompting, encouragement, and motivation, I would have had a tremendous amount of additional free time and sanity.

About the Reviewer

Krzee King is a self taught BSD/Linux user. He began helping in the OpenVPN community in 2007, when he and the author Eric took control of the IRC channel, and later founded the web forum with Eric and dougy. He believes very strongly in the importance of encryption, and the need for strong encryption to be usable by all. He also had the pleasure of reviewing OpenVPN 2 Cookbook by Jan Just Keijser.

Thanks to my lovely wife and my parents, for their endless support. I love you guys.

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Preface

OpenVPN is arguably the best cross-platform secure networking technology currently available. The development community is large and active every day of the year, with new developers popping up regularly with patches and feature requests. It is not only used by hobbyists, but also by for-pay VPN providers strewn about the Internet.

In Troubleshooting OpenVPN, we identify the most common problems and pitfalls in the deployment of OpenVPN. We demonstrate where and how to use an assortment of diagnostic and investigative tools, both common and lesser known.

By the end of this book, you should be able to understand and identify where a problem resides, both within your VPN infrastructure and also from external causes. The log file is fully detailed and you will be able to leverage the varying logging levels to suit your troubleshooting efforts.

What this book covers

Chapter 1, Troubleshooting Basics, helps the reader break down problems into digestible portions with related components. Some of the concepts discussed include generic techniques useful in more than just OpenVPN problem solving.

Chapter 2, Common Problems, will identify the issues seen most frequently by both novice administrators and experienced administrators alike.

Chapter 3, Installing OpenVPN, covers compilation and installation of OpenVPN on a variety of platforms. Virtual network adapters, alternative client packages, and software dependencies will be identified.

Chapter 4, The Log File, focuses heavily on the OpenVPN log file and how to adjust and decipher the verbosity of the available messages. This is an extremely valuable resource when identifying and correcting problems.

Chapter 5, Client and Server Startup, discusses software and system dependencies necessary for process startup. Items like file permissions, scripting, and basic networking all contribute to successfully running OpenVPN.

Chapter 6, Certificates and Authentication, illustrates the varying authentication paths and where breakage can occur. System time, authentication backends and scripting are all addressed.

Chapter 7, Network and Routing, shows where network topology and routing bring complexity to the OpenVPN architecture. Conflicting routes, address inconsistency, and subnetting will all be covered.

Chapter 8, Performance, was written to help you identify performance bottlenecks and places where efficiencies can be improved.

Chapter 9, External Problems, covers where and when problems can exist outside your OpenVPN infrastructure, and even entirely outside your network or control.

What you need for this book

This book was written with the VPN administrator in mind. Many of the examples within leverage both the server and client sides of a connection, and lack of control at the server end will prove frustrating. I am assuming you either have access to a server, or have the means to create a functioning server, with your operating system of choice.

Examples within this book are focused primarily on Linux or BSD command-line tools, but there are a number of Windows examples interspersed within the content. To make the most of your time, try to have the following available:

An OpenVPN server, ideally running on Linux or FreeBSD

An OpenVPN client, running any operating system you choose

The ability to install software on and connect to the OpenVPN server without OpenVPN running

Who this book is for

An OpenVPN server administrator is most likely to use this book to its potential. Enterprising VPN users may also be able to use the techniques and applications described within to their own benefit, however. Much of this title covers basic troubleshooting skills that can be leveraged in nearly any situation, not just with OpenVPN.

Conventions

In this book, you will find a number of text styles that distinguish between different kinds of information. Here are some examples of these styles and an explanation of their meaning.

Code words in text, database table names, folder names, filenames, file extensions, pathnames, dummy URLs, user input, and Twitter handles are shown as follows: The --auth-user-pass-verify script is the last in a long chain of scripts that are run.

Any command-line input or output is written as