Cisco OL-5490-01 User manual

Corporate Headquarters
Cisco Systems, Inc.
170 West Tasman Drive
San Jose, CA 95134-1706
USA
http://www.cisco.com
Tel: [phone]
800 553-NETS (6387)
Fax: [phone]
VPN Client User Guide for Mac OS X
Release 4.6
August 2004
Customer Order Number:
Text Part Number: OL-5490-01

THE SPECIFICATIONS AND INFORMATION REGARDING THE PRODUCTS IN THIS MANUAL ARE SUBJECT TO CHANGE WITHOUT NOTICE. ALL
STATEMENTS, INFORMATION, AND RECOMMENDATIONS IN THIS MANUAL ARE BELIEVED TO BE ACCURATE BUT ARE PRESENTED WITHOUT
WARRANTY OF ANY KIND, EXPRESS OR IMPLIED. USERS MUST TAKE FULL RESPONSIBILITY FOR THEIR APPLICATION OF ANY PRODUCTS.
THE SOFTWARE LICENSE AND LIMITED WARRANTY FOR THE ACCOMPANYING PRODUCT ARE SET FORTH IN THE INFORMATION PACKET THAT
SHIPPED WITH THE PRODUCT AND ARE INCORPORATED HEREIN BY THIS REFERENCE. IF YOU ARE UNABLE TO LOCATE THE SOFTWARE LICENSE
OR LIMITED WARRANTY, CONTACT YOUR CISCO REPRESENTATIVE FOR A COPY.
The Cisco implementation of TCP header compression is an adaptation of a program developed by the University of California, Berkeley (UCB) as part of UCB’s public
domain version of the UNIX operating system. All rights reserved. Copyright © 1981, Regents of the University of California.
NOTWITHSTANDING ANY OTHER WARRANTY HEREIN, ALL DOCUMENT FILES AND SOFTWARE OF THESE SUPPLIERS ARE PROVIDED “AS IS” WITH
ALL FAULTS. CISCO AND THE ABOVE-NAMED SUPPLIERS DISCLAIM ALL WARRANTIES, EXPRESSED OR IMPLIED, INCLUDING, WITHOUT
LIMITATION, THOSE OF MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT OR ARISING FROM A COURSE OF
DEALING, USAGE, OR TRADE PRACTICE.
IN NO EVENT SHALL CISCO OR ITS SUPPLIERS BE LIABLE FOR ANY INDIRECT, SPECIAL, CONSEQUENTIAL, OR INCIDENTAL DAMAGES, INCLUDING,
WITHOUT LIMITATION, LOST PROFITS OR LOSS OR DAMAGE TO DATA ARISING OUT OF THE USE OR INABILITY TO USE THIS MANUAL, EVEN IF CISCO
OR ITS SUPPLIERS HAVE BEEN ADVISED OF THE POSSIBILITY OF SUCH DAMAGES.
VPN Client User Guide for Mac OS X
Copyright © 2004, Cisco Systems, Inc.
All rights reserved.
CCIP, CCSP, the Cisco Arrow logo, the Cisco Powered Network mark, Cisco Unity, Follow Me Browsing, FormShare, and StackWise are trademarks of Cisco Systems, Inc.;
Changing the Way We Work, Live, Play, and Learn, and iQuick Study are service marks of Cisco Systems, Inc.; and Aironet, ASIST, BPX, Catalyst, CCDA, CCDP, CCIE, CCNA,
CCNP, Cisco, the Cisco Certified Internetwork Expert logo, Cisco IOS, the Cisco IOS logo, Cisco Press, Cisco Systems, Cisco Systems Capital, the Cisco Systems logo,
Empowering the Internet Generation, Enterprise/Solver, EtherChannel, EtherSwitch, Fast Step, GigaStack, Internet Quotient, IOS, IP/TV, iQ Expertise, the iQ logo, iQ Net
Readiness Scorecard, LightStream, MGX, MICA, the Networkers logo, Networking Academy, Network Registrar, Packet, PIX, Post-Routing, Pre-Routing, RateMUX, Registrar,
ScriptShare, SlideCast, SMARTnet, StrataView Plus, Stratm, SwitchProbe, TeleRouter, The Fastest Way to Increase Your Internet Quotient, TransPath, and VCO are registered
trademarks of Cisco Systems, Inc. and/or its affiliates in the U.S. and certain other countries.
All other trademarks mentioned in this document or Web site are the property of their respective owners. The use of the word partner does not imply a partnership relationship
between Cisco and any other company. (0304R)

iii
VPN Client User Guide for Mac OS X
OL-5490-01
CONTENTS
About This Guide vii
Audience vii
Contents vii
Related Documentation viii
Terminology viii
Document Conventions viii
Data Formats ix
Obtaining Documentation ix
Cisco.com ix
Documentation CD-ROM ix
Ordering Documentation x
Documentation Feedback x
Obtaining Technical Assistance x
Cisco.com x
Technical Assistance Center xi
Cisco TAC Website xi
Cisco TAC Escalation Center xii
Obtaining Additional Publications and Information xii
CHAPTER 1Understanding the VPN Client 1-1
Connection Technologies 1-1
VPN Client Overview 1-2
VPN Client Features 1-3
Program Features 1-3
Authentication Features 1-5
IPSec Features 1-5
VPN Client IPSec Attributes 1-6
CHAPTER 2Installing the VPN Client 2-1
Verifying System Requirements 2-1
Gathering Information You Need 2-1
Obtaining the VPN Client Software 2-2
Preconfiguring the VPN Client 2-2

Contents
iv
VPN Client User Guide for Mac OS X
OL-5490-01
Preconfiguring the User Profile 2-3
Preconfiguring the Global Profile 2-3
Bundling a Root Certificate with the Installation Package for Darwin 2-4
Installing the VPN Client 2-4
Authentication 2-4
VPN Client Installation Process 2-6
Introduction 2-6
Accepting the License Agreement 2-7
Selecting the Application Destination 2-7
Choosing the Installation Type 2-8
CLI Version Install Script Notes 2-12
Uninstalling the VPN Client 2-12
CHAPTER 3Navigating the User Interface 3-1
VPN Client Menu 3-1
Choosing a Run Mode 3-2
Operating in Simple Mode 3-2
VPN Client Window—Simple Mode 3-2
Main Menus—Simple Mode 3-3
Connection Entries Menu 3-3
Status Menu 3-3
Operating in Advanced Mode 3-4
VPN Client Window—Advanced Mode 3-4
Toolbar Action Buttons—Advanced Mode 3-5
Main Tabs—Advanced Mode 3-5
Main Menus—Advanced Mode 3-6
Connection Entries Menu 3-6
Status Menu 3-7
Certificates Menu 3-7
Log Menu 3-8
Right-Click Menus 3-8
Connection Entries Tab Right-Click Menu 3-9
Certificates Tab Right-Click Menu 3-10
CHAPTER 4Configuring Connection Entries 4-1
Creating a Connection Entry 4-1
Authentication Methods 4-3
Group Authentication 4-3

Contents
v
VPN Client User Guide for Mac OS X
OL-5490-01
Mutual Group Authentication 4-4
Certificate Authentication 4-4
Transport Parameters 4-6
Enable Transport Tunneling 4-7
Transparent Tunneling Mode 4-7
Allow Local LAN Access 4-7
Peer Response Timeout 4-8
Backup Servers 4-8
CHAPTER 5Establishing a VPN Connection 5-1
Checking Prerequisites 5-1
Establishing a Connection 5-1
Connecting to a Default Connection Entry 5-3
Choosing Authentication Methods 5-3
Shared Key Authentication 5-3
VPN Group Name and Password Authentication 5-4
RADIUS Server Authentication 5-4
SecurID Authentication 5-5
Using Digital Certificates 5-6
CHAPTER 6Enrolling and Managing Certificates 6-1
Using the Certificate Store 6-1
Enrolling Certificates 6-2
Managing Enrollment Requests 6-5
Viewing the Enrollment Request 6-5
Deleting an Enrollment Request 6-5
Changing the Password on an Enrollment Request 6-6
Retrying an Enrollment Request 6-6
Importing a Certificate 6-7
Viewing a Certificate 6-7
Exporting a Certificate 6-9
Deleting a Certificate 6-10
Verifying a Certificate 6-11
Changing the Password on a Personal Certificate 6-12

Contents
vi
VPN Client User Guide for Mac OS X
OL-5490-01
CHAPTER 7Managing the VPN Client 7-1
Managing Connection Entries 7-1
Importing a Connection Entry 7-1
Modifying a Connection Entry 7-2
Deleting a Connection Entry 7-3
Event Logging 7-4
Enable Logging 7-4
Clear Logging 7-5
Set Logging Options 7-5
Opening the Log Window 7-7
Viewing Statistics 7-8
Tunnel Details 7-9
Route Details 7-10
Notifications 7-11
I NDEX

vii
VPN Client User Guide for Mac OS X
OL-5490-01
About This Guide
This VPN Client User Guide describes how to install, use, and manage the Cisco VPN Client for the
Macintosh operating system, Version 10.2 or later. You can manage the VPN Client for Mac OS X from
the graphical user interface or from the command-line interface.
The VPN Client for Mac OS X installer program installs both the graphical user interface and the
command-line version of the VPN Client.
Audience
This guide is for remote clients who want to set up virtual private network (VPN) connections to a central
site. Network administrators can also use this guide for information about configuring and managing
VPN connections for remote clients. You should be familiar with the Macintosh platform and know how
to use Macintosh applications. Network administrators should be familiar with Macintosh system
configuration and management and know how to install, configure, and manage internetworking
systems.
Contents
This guide contains the following chapters:
•Chapter 1, “Understanding the VPN Client.” This chapter describes how the VPN Client software
works and lists the main features.
•Chapter 2, “Installing the VPN Client.” This chapter describes how to install the VPN Client
software application.
•Chapter 3, “Navigating the User Interface.” This chapter describes the main VPN Client window
and the tools, tabs, menus and icons for navigating the user interface.
•Chapter 4, “Configuring Connection Entries.” This chapter describes how to configure VPN Client
connection entries, including optional parameters.
•Chapter 5, “Establishing a VPN Connection.” This chapter describes how to connect to a private
network using the VPN Client, an Internet connection, and the user authentication methods
supported by the VPN Client.
•Chapter 6, “Enrolling and Managing Certificates.” This chapter describes how to obtain digital
certificates to use for authentication and how to manage these certificates in the VPN Client
certificate store.

viii
VPN Client User Guide for Mac OS X
OL-5490-01
About This Guide
Related Documentation
•Chapter 7, “Managing the VPN Client.” This chapter describes how to manage VPN Client
connections, use the event log, and view tunnel details, including packet and routing data.
Related Documentation
The following is a list of user guides and other documentation related to the VPN Client for Mac OS X
and the VPN devices that provide the connection to the private network.
•Release Notes for the Cisco VPN Client, Release 4.6
•Cisco VPN Client Administrator Guide, Release 4.6
•Cisco VPN 3000 Series Concentrator Getting Started Guide, Release 4.6
•Cisco VPN 3000 Series Concentrator Reference Volume I: Configuration, Release 4.1
•Cisco VPN 3000 Series Concentrator Reference Volume II: Administration and Monitoring, Release
4.1
Terminology
In this user guide:
•The term Cisco VPN device refers to the following Cisco products:
– Cisco IOS devices that support Easy VPN server functionality
– Cisco VPN 3000 Series Concentrators
– Cisco PIX Firewall Series
•The term “PC” refers generically to any personal computer.
•The term click means click the left button on a normally-configured multi-button mouse. The term
right-click means click the right button on a normally-configured multi-button mouse. If your mouse
has only one button, use Ctrl-Click to access the right-click menus.
Document Conventions
This guide uses the following typographic conventions:
•Boldface font—Describes user actions and commands.
•Italic font—Describes arguments that you supply the values for.
•Screen font—Describes terminal sessions and information displayed by the system.
•Boldface screen font—Describes information that you must enter.
Notes use the following conventions:
Note Means reader take note. Notes contain helpful suggestions or references to material not covered in the
publication.
Cautions use the following conventions:

ix
VPN Client User Guide for Mac OS X
OL-5490-01
About This Guide
Obtaining Documentation
Caution Means reader be careful. Cautions alert you to actions or conditions that could result in equipment
damage or loss of data.
Data Formats
When you configure the VPN Client, enter data in these formats unless the instructions indicate
otherwise.
•IP Address—Use standard 4-byte dotted decimal notation (for example, 192.168.12.34). You can
omit leading zeros in a byte position.
•Hostnames—Use legitimate network host or end-system name notation (for example, VPN01).
Spaces are not allowed. A hostname must uniquely identify a specific system on a network. A
hostname can be up to 255 characters in length.
•User names and Passwords—Text strings for user names and passwords use alphanumeric characters
in both upper- and lower-case. Most text strings are case sensitive. For example, simon and Simon
would represent two different user names. The maximum length of user names and passwords is
generally 32 characters, unless specified otherwise.
Obtaining Documentation
Cisco provides several ways to obtain documentation, technical assistance, and other technical
resources. These sections explain how to obtain technical information from Cisco Systems.
Cisco.com
You can access the most current Cisco documentation on the World Wide Web at this URL:
http://www.cisco.com/univercd/home/home.htm
You can access the Cisco website at this URL:
http://www.cisco.com
International Cisco web sites can be accessed from this URL:
http://www.cisco.com/public/countries_languages.shtml
Documentation CD-ROM
Cisco documentation and additional literature are available in a Cisco Documentation CD-ROM
package, which may have shipped with your product. The Documentation CD-ROM is updated monthly
and may be more current than printed documentation. The CD-ROM package is available as a single unit
or through an annual subscription.
Registered Cisco.com users can order the Documentation CD-ROM (product number
DOC-CONDOCCD=) through the online Subscription Store:
http://www.cisco.com/go/subscription

x
VPN Client User Guide for Mac OS X
OL-5490-01
About This Guide
Obtaining Technical Assistance
Ordering Documentation
You can find instructions for ordering documentation at this URL:
http://www.cisco.com/univercd/cc/td/doc/es_inpck/pdi.htm
You can order Cisco documentation in these ways:
•Registered Cisco.com users (Cisco direct customers) can order Cisco product documentation from
the Networking Products MarketPlace:
http://www.cisco.com/en/US/partner/ordering/index.shtml
•Registered Cisco.com users can order the Documentation CD-ROM (Customer Order Number
DOC-CONDOCCD=) through the online Subscription Store:
http://www.cisco.com/go/subscription
•Nonregistered Cisco.com users can order documentation through a local account representative by
calling Cisco Systems Corporate Headquarters (California, U.S.A.) at 408 526-7208 or, elsewhere
in North America, by calling 800 553-NETS (6387).
Documentation Feedback
You can submit comments electronically on Cisco.com. On the Cisco Documentation home page, click
Feedback at the top of the page.
You can e-mail your comments to b[email protected].
You can submit your comments by mail by using the response card behind the front cover of your
document or by writing to the following address:
Cisco Systems
Attn: Customer Document Ordering
170 West Tasman Drive
San Jose, CA 95134-9883
We appreciate your comments.
Obtaining Technical Assistance
Cisco provides Cisco.com, which includes the Cisco Technical Assistance Center (TAC) Website, as a
starting point for all technical assistance. Customers and partners can obtain online documentation,
troubleshooting tips, and sample configurations from the Cisco TAC website. Cisco.com registered users
have complete access to the technical support resources on the Cisco TAC website, including TAC tools
and utilities.
Cisco.com
Cisco.com offers a suite of interactive, networked services that let you access Cisco information,
networking solutions, services, programs, and resources at any time, from anywhere in the world.
Cisco.com provides a broad range of features and services to help you with these tasks:
•Streamline business processes and improve productivity
•Resolve technical issues with online support