PGP 7.0 for Macintosh User guide

Category
Software
Type
User guide
PGP Freeware
for MacOS
User’s Guide
Version 7.0
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User’s Guide 5
Table of Contents
Part I: Overview
Preface.....................................................13
OrganizationofthisGuide.........................................14
HowtocontactPGPSecurityandNetworkAssociates .................16
Customerservice............................................16
Technical support ...........................................16
NetworkAssociatestraining...................................16
Comments and feedback . . . . . . . . ..............................17
Recommended readings . . . . . . . . . . . . ..............................17
Thehistoryofcryptography ...................................17
Technicalaspectsofcryptography .............................17
Politicsofcryptography ......................................19
Networksecurity ............................................20
Chapter1. PGPBasics .......................................21
PGPaspartofyoursecuritystructure...............................21
PGPfeatures ....................................................22
BasicstepsforusingPGP.........................................23
Chapter 2. A Quick Tour of PGP . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .25
PGPtools .......................................................26
PGP within supported email applications . . . . . . . . . . . . . . ..............26
PGPmenu.......................................................27
ThePGPcontextualmenu,andothershortcuts .......................28
GettingHelp.....................................................28
Table of Contents
6 PGP Freeware
Part II: Working with Keys
Chapter3. MakingandExchangingKeys ........................31
Key”concepts..................................................31
Makingakeypair ................................................32
Creatingapassphrasethatyouwillremember ........................38
Changingyourkeypair ...........................................39
Backingupyourkeys.............................................39
Protectingyourkeys .............................................40
WhatifIforgetmypassphraseorlosemykey? .......................40
WhatisPGPkeyreconstruction?...............................41
Exchangingpublickeyswithothers.................................43
Distributingyourpublickey ...................................43
Placingyourpublickeyonakeyserver .....................43
Includingyourpublickeyinanemailmessage ...............44
Exportingyourpublickeytoafile..........................45
Obtainingthepublickeysofothers.............................45
Gettingpublickeysfromakeyserver.......................46
Gettingpublickeysfromemailmessages ...................48
Importing keys . . . . . . . . . . . . ..............................48
Verifyingtheauthenticityofakey ..............................49
Whyverifytheauthenticityofakey? .......................49
Verifywithadigitalfingerprint.............................50
Validatingapublickey........................................50
Workingwithtrustedintroducers...............................50
Whatisatrustedintroducer?..............................51
What is a meta-introducer? . ..............................51
Chapter4. ManagingKeys ....................................53
ManagingyourPGPkeyrings ......................................53
ThePGPkeyswindow ........................................54
PGPkeysattributedefinitions..............................54
Specifying a default key pair on your PGP keyring . . . . . . . . . . . .58
Importing and exporting keys on your PGP keyring . . . . . . . . . . .58
Deleting a key or signature on your PGP keyring . . . . . . . . . . . . .58
User’s Guide 7
Table of Contents
DisablingandenablingkeysonyourPGPkeyring ............59
Examiningandsettingkeyproperties ...........................60
Generalkeyproperties ...................................60
Subkeys properties . . . . . . . . ..............................70
Designatedrevokerproperties.............................73
AdditionalDecryptionKeyproperties.......................75
AddinganX.509certificatetoyourPGPkey......................76
Splittingandrejoiningkeys ...................................80
Creatingasplitkey ......................................81
Rejoiningsplitkeys......................................83
Updatingyourkeyonakeyserver..............................87
Reconstructingyourkey ......................................89
Part III: Securing Your Files and Communications
Chapter5. SecuringEmail ....................................93
Securing email communications . . . . . . ..............................93
PGP/MIME ..................................................93
Encryptingandsigningemail..................................94
Encrypting and signing email using the PGP plug-ins . . . . . . . . .94
Encrypting and signing email without PGP plug-in support . . . . .98
Encryptingemailtogroupsofrecipients ....................99
Decryptingandverifyingemail................................102
Decrypting and verifying email using the PGP plug-ins . . . . . . .102
Decrypting and verifying email without PGP plug-in support . . .103
Chapter6. SecuringFiles ....................................105
SecuringyourfilesandfolderswithPGP ...........................105
Encryptingandsigningfiles..................................105
Decryptingandverifyingfiles.................................108
Openingaself-decryptingarchive.........................108
Signinganddecryptingfileswithasplitkey .........................108
Permanentlyerasingfilesandfreediskspace .......................109
UsingPGPWipetopermanentlydeleteafile ....................110
Using the PGP Wipe Free Space Wizard to clean free disk space . . .111
Schedulingfolderandfreespacewiping .......................112
Table of Contents
8 PGP Freeware
Part IV: Securing Your Network Communications with PGPnet
Chapter7. PGPnetBasics....................................117
Learning about PGPnet ..........................................117
WhatisaVirtualPrivateNetwork? .................................118
VPNterms .................................................119
Chapter 8. A Quick Tour of PGPnet . . . . . . . . . . . . . . . . . . . . . . . . . . . .121
DisplayingPGPnet ..............................................121
TurningPGPnetonandoff .......................................121
QuittingPGPnet ............................................122
PGPnetfeatures ................................................122
PGPmenusicon ................................................123
The PGPnet window (at a glance) . . . . . .............................123
Menus ....................................................123
Panels ....................................................124
Statusbar .................................................125
ReviewingthestatusofexistingSAs ...............................126
EstablishingandterminatingSAs..................................128
Openingahostlist..........................................128
Savingahostlist ...........................................129
Blocking communications with other machines . . . . . . . . . .............129
Blocking a host and tracing the source of communications . . . . . . . .131
Tracinganattacker .........................................131
Removingahostfromthelistofblockedhosts..................132
ReviewingPGPnetslogentries ...................................133
ChangingyoursecureTCP/IPconfigurations ........................134
Chapter9. ConfiguringPGPnetsVPNFeature...................135
ConfiguringPGPnetsVPNfeature.................................136
Step1.DisplayingPGPnet ...................................136
Step2.SecuringyourTCP/IPconfigurations ....................136
Step3.Selectingyourauthenticationkeyorcertificate............137
Step 4a. Importing a host list . . . . .............................138
Step 4b. Adding a host, subnet, or gateway . . . . . . . . .............139
User’s Guide 9
Table of Contents
Step5.EstablishinganSA ...................................139
UsingtheHost/Gatewaydialogbox ................................140
Whatyouneedtoknow......................................141
Adding a host, subnet, or gateway . . . . . . . . . . . . . . . .............141
Modifyingahost,subnet,orgatewayentry..........................144
Removing a host, subnet, or gateway entry . . . . . . . . . . . . . .............144
SharedSecret..............................................145
RemoteAuthentication ......................................145
Requiring a host to present a specific key or certificate . . . . . . .145
Authenticationtype.....................................147
UsingAggressiveMode......................................148
Part V: Appendices and Glossary
AppendixA. SettingPreferences..............................151
SettingPGPpreferences .........................................151
Settinggeneralpreferences ..................................152
Settingfilepreferences ......................................155
Settingemailpreferences ....................................156
Settingmenupreferences ....................................158
Settingserverpreferences ...................................161
Accessing HTTP servers through a proxy server . . . . . . . . . . . .164
Settingcertificateauthoritypreferences ........................165
Settingadvancedpreferences ................................166
SettingVPNpreferences .....................................169
Settingautomatickeyrenewalvalues......................171
SettingVPNauthenticationpreferences ........................172
SettingVPNadvancedpreferences ............................174
Adding and removing Allowed Remote proposals . . . . . . . . . . . .179
WorkingwithIKEandIPsecproposals.....................179
Appendix B. Troubleshooting PGP . . . . . . . . . . . . . . . . . . . . . . . . . . . .183
Table of Contents
10 PGP Freeware
Appendix C. Troubleshooting PGPnet . . . . . . . . . . . . . . . . . . . . . . . . . .187
PGPneterrormessages ..........................................187
Additionaltips..................................................188
Understandingauthentication.....................................189
TheVPNAuthenticationpanel ................................189
Host/Gatewaydialog:RemoteAuthentication ...................190
Appendix D. Transferring Files Between the MacOS and Windows . .191
Sending from the MacOS to Windows . .............................192
ReceivingWindowsfilesontheMacOS.............................194
Supportedapplications ......................................194
AppendixE. BiometricWordLists.............................197
BiometricWordLists ............................................197
Glossary...................................................203
Index......................................................215
Part I: Overview
•Preface
Chapter 1: PGP Basics
Chapter 2: A Quick Tour of PGP
User’s Guide 13
Preface
PGP is part of your organization’s security toolkit for protecting one of your
most important assets: information. Corporations have traditionally put locks
on their doors and file cabinets and require employees to show identification
to prove that they are permitted access into various parts of the busin ess site.
PGP is a valuable tool to help you protect the security and integrity of your
organization’sdataand messages.Formanycompanies, lossofconfidentiality
meanslossofbusiness.
This guide describ es how to use PG P
®
Freeware for the Macintosh. PGP
Freeware (also referred to in this docu ment simply as PGP) has many new
features, which are descri bed in the ReadMe.txt file that accompanies the
product.
NOTE: If you are new to cryptography a nd would like an overview of
the terminology and concepts you will encounter while using PGP, see
An Introduction to Cryptography, which is included with the product.
Preface
14 PGP Freeware
Organization of this Guide
This Guide is divided into the following parts and chapters:
Part I, “The Basics”
This section introduces you to the features of PGP and gives you a quick look
at the PGP user i nterface. Part I includes the following chapters:
Chapter 1, PGP Basics,” provides an overview of thecapabilities of PGP
and how PGP fits into the larger security structure of an organization.
Chapter 2, “A Quick Tour of PGP,” provides you with a brief
introduction to accessing PGP utilities from your desktop.
Part II, “Working With Keys”
This section introduces the important concept of keys,whicharefundamental
to data encryption. Part II includes the following chapters:
Chapter 3, “Making and Exchanging Keys,” explains the concept of a
data encryption key and describes how you create, protect, exchange,
and validate keys.
Chapter 4, “Managing Keys,” provides you with more details of key
maintenance,includingmanaging yourkeyring,examiningandchanging
key properties, creating split keys.
Part III “Securing Your Files and Communications”
This section explains how to use your data encryption keys to secure data that
you send from or store on your computer. Part III includes the following
chapters:
Chapter5, “SecuringEmail,”describes howtosend encryptedemail,and
how t o decrypt and verify email you receive.
Chapter 6, “Securing Files,” describes how to use PGP to securely
maintain files, either for email or for storage on your computer.
Part IV, “Securing Your Network Communications with PGPnet”
This section describes the features of PGPnet, a PGP tool that enables you to
create Virtual Private Networks (VPNs) with trusted users not directly
connected to your network. The chapters of Part IV also guide you through
configuring the features of PGPnet to customize the security of your
workstation. Part IV includes the following chapters:
Chapter 7, “PGPnet Basics,” gives you an overview of Virtual Private
Networks.
User’s Guide 15
Preface
Chapter8,“AQuickTourof PGPnet,”introduces you to aspects of PGP’s
user interface that are related to PGPnet.
Chapter 9, “Configuring PGPnet’s VPN Feature,” describes how to use
PGPnet to set up and customize a Virtual Private Network (VPN).
Part V, “Appendices and Glossary”
This section includes information on how to further customize PGP on your
computer, as well as troubleshooting tips should you encounter problems
using PGP. A Glossary is included as a convenient reference spot where you
will find definitions of terms related to network security. Part V includes the
following appendices:
Appendix A, “Setting Preferences,” explains how to use the Preferences
dialog box to create a version of PGP on your computer that best suits
your needs.
Appendix B, “Troubleshooting PGP,” guides you in solving problems
you may encounter when using PGP.
AppendixC, “TroubleshootingPGPnet,” guidesyouin solvingproblems
you may encounter when using PGP’s PGPnet feature.
Appendix D, “Transferring Files Between the MacOS and Windows,”
explains how PGP translates files that are sent between two systems
when one system operates using a Mac operating system (OS) and the
othersystemoperatesusingaWindowsOS.
Appendix E, “Biometric Word Lists,” explains biometric word lists and
how t hey are used by PGP.
Glossary,page 203,provides you withdefinitions formanyt erms related
to PGP and network security.
Preface
16 PGP Freeware
How to contact PGP Security and Network
Associates
Customer service
Network Associates continues to market and support the product lines from
each of the new independent business units. You may direct all questions,
comments, or requests concerning the software you purchased, your
registration status, or similar issues to the Network Associates Customer
Service department at the following address:
Network Associates Customer Service
4099 McEwen, Suite 500
Dallas, Texas 75244
U.S.A.
The department’s hours of operation are 8
A.M.to8P.M. Central time, Monday
through Friday.
Other contact information for corporate-licensed customers:
Other contact information for retail-licensed customers:
Technical support
Network Associates does not provide technical supportfor f reeware products.
Network Associates training
For information about scheduling on-site training for any PGP Security or
Network Associates product, call Network Associates Customer Service at:
(972) 308-9960.
Phone: (972) 308-9960
E-Mail: services_corporate_division@nai.com
World Wide Web: http://support.nai.com
Phone: (972) 308-9960
E-Mail: cust_care@nai.com
World Wide Web: http://www.pgp.com/
User’s Guide 17
Preface
Comments and feedback
PGP Security appreciates your comments and reserves the right to use any
information you supply in any way it believes appropriate without incurring
any obligation whatsoever. Please send any documentation comments to
tns_documentation@nai.com.
Recommended readings
This section identif ies Web sites, books, and periodicals abo ut the history,
technical aspects, and politics of cryptography, as well as trusted PGP
download sites.
The history of cryptography
The C ode Book: The Evolution of Secrecy from Mary, Queen of Scots, to Quantum
Cryptography,SimonSingh,Doubleday&Company,Inc.,1999,ISBN
0-385-49531-5.
The Codebreakers: The Story of Secret Writing,DavidKahn,Simon&Schuster
Trade,1996,ISBN0-684-83130-9(updatedfrom the1967edition).Thisbook
is ahistory ofcodes and code breakersfrom the time of theEgyptiansto the
end of WWII. Kahn first wrote it in the sixties—this is the revised edition.
This book won't teach you anything about how cryptography is done, but
it has been the inspiration of the whole modern generation of
cryptographers.
Technical aspects of cryptography
Web sites
www.iacr.org—International Association for Cryptologic Research
(IACR). The IACR holds cryptographic conferences and publishes journals.
www.pgpi.org
—An international PGP Web site, which is not maintained
by PGP Security, Inc. or Network Associates, Inc., is an unofficial yet
comprehensive resource for PGP.
www.nist.gov/aes
—The National Institute of Standards and Technology
(NIST) Advanced Encryption Standard (AES) Development Effort,
perhaps t he most interesting project going on in cryptography today.
www.ietf.org/rfc/rfc2440.txt
—The specification for the IETF OpenPGP
standard.
Preface
18 PGP Freeware
Books and periodicals
AppliedCryptography:Protocols,Algorithms,and SourceCodein C,2
nd
edition,
Bruce Schneier, John Wiley & Sons, 1996; ISBN 0-471-12845-7. If you can
only buy one book to get s tarted in cryptography, this is the one to buy.
Handbook of Applied Cryptography, Alfred Menezes, Paul van Oorschot and
Scott Vanstone, CRC Press, 1996; ISBN 0-8493-8523-7. This is the technical
bookyou shouldget afterSchneier. Thereis alot ofheavy-duty mathin this
book, but it is nonetheless usable for those who do not understand the
math.
Journal of Cryptology, International Association for Cryptologic Research
(IACR). S ee www.iacr.org
.
Advances in Cryptology, conference proceedings of the IACR CRYPTO
conferences, published yearly by Springer-Verlag. See www.iacr.org
.
Cryptography for the Internet, Philip Zimmermann, Scientific American,
October 1998 (introductory tutorial article).
The Twofish Encryption Algorithm: A 128-Bit Block Cipher, Bruce Schneier, et
al, John Wiley & Sons, Inc., 1999; ISBN: 0471353817. Contains details about
the Twofish cipher ranging from design criteria to cryptanalysi s of the
algorithm.
User’s Guide 19
Preface
Politics of cryptography
Web sites
www.epic.org—Electronic Privacy Information Center.
www.crypto.org
—Internet Privacy Coalition.
www.eff.org
—Electronic Frontier Foundation.
www.privacy.org
—The Privacy Page. Great information resource a bout
privacy issues.
www.cdt.org
—Center for Democracy and Technology.
www.pgp.com/phil
—Phil Zimmermann’s home page, his Senate
testimony, and so on.
Books
Privacy on the Line: The Politics of Wiretapping and Encryption, Whitfield
Diffie and Susan Landau, The MIT Press, 1998, ISBN 0-262-04167-7. This
book is a discussion of the history and policy surrounding cryptography
and communications security. It is an excellent read, even for beginners
and non-technical people. Includes information that even a lot of experts
don’t know.
Technology and Privacy: The New Landscape, Philip Agre and Marc
Rotenberg, The MIT Press, 1997;ISBN 0-262-01162-x.
Building in Big Brother, The Cryptographic Policy Debate, edited by Lance
Hoffman, Springer-Verlag, 1995; ISBN 0-387-94441-9.
The Official PGP User’s Guide, Philip Zimmermann, The MIT Press, 1995;
ISBN 0-262-74017-6. How to use PGP, written in Phil’s own w ords.
The Code Book: The Evolution of Secrecy from Ancient Egypt to Quantum
Cryptography, Simon Singh, Doubleday & Company, Inc., September 2000;
ISBN: 0385495323. This book is an excellent primer for those wishing to
understand how the human n eed for privacy has m anifested itself through
cryptography.
Preface
20 PGP Freeware
Network security
Books
Building Internet Firewalls, Elizabeth D. Zwicky, D. Brent Chapman, Simon
Cooper, and Deborah Russell (Editor), O’Reilly & Associates, Inc., 2000;
ISBN:1565928717. This bookis a practicalguideto designing,building,and
maintaining firewalls.
Firewalls and Internet Security: Repelling the Wily Hacker, William R.
Cheswick,S teven M. Bellovin, Addison WesleyLongman, Inc.,1994; ISBN:
0201633574. This book is a practical guide to protecting networks from
hacker attacks through the Internet.
Hacking Exposed: Network Security Secrets and Solutions, Stuart McClure, Joel
Scambray, and George Kurtz, The McGraw-Hill Companies, 1999; ISBN:
0072121270. The state of the art in breaking into computers and networks,
as viewed from the vantage point of the attacker and the defender.
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PGP 7.0 for Macintosh User guide

Category
Software
Type
User guide

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