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Contents
Overview 1
Lesson: Introduction to Cryptography 3
Lesson: Working with Digital Certificates 15
Lab 8.1: Obtaining a Server Certificate 35
Lesson: Using the Secure Sockets
Layer/Transport Layer Security Protocols 39
Lesson: Using Internet Protocol Security 58
Review 63
Lab 8.2: ProtectingCommunication
Privacy andDataIntegrity 65
Course Evaluation 76
Module 8:Protecting
Communication Privacy
and DataIntegrity
Information in this document, including URL and other Internet Web site references, is subject to
change without notice. Unless otherwise noted, the example companies, organizations, products,
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otherwise), or for any purpose, without the express written permission of Microsoft Corporation.
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license to these patents, trademarks, copyrights, or other intellectual property.
2002 Microsoft Corporation. All rights reserved.
Microsoft, MS-DOS, Windows, Windows NT, ActiveX, Active Directory, Authenticode, Hotmail,
JScript, Microsoft Press, MSDN, PowerPoint, Visual Basic, Visual C++, Visual Studio, and
Windows Media are either registered trademarks or trademarks of Microsoft Corporation in the
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The names of actual companies and products mentioned herein may be the trademarks of their
respective owners.
Module8:ProtectingCommunicationPrivacyandDataIntegrity iii
Instructor Notes
This module provides students with an overview of cryptography and digital
certificates. The module then explains how students can protect dataand
communications between the Web browser and the Web server. After
completing this module, students will be able to protect the portions of a Web
application that require private communications through Secure Sockets Layer
(SSL) security.
After completing this module, students will be able to:
!
Define the basic elements of cryptography.
!
Describe the purpose of digital certificates and obtain one through a
Certificate Authority (CA).
!
Validate user and Web server identity through the use of SSL/Transport
Layer Security (TLS).
!
Protect communications between Web application resources through the use
of Internet Protocol security (IPSec).
To teach this module, you need the following materials:
!
Microsoft
®
PowerPoint
®
file 2300A_08.ppt
!
Hypertext Markup Language (HTML) and Flash animation files
2300A_08_A05_1619.htm and 2300A_08_A05_1619.swf
To prepare for this module:
!
Read all of the materials for this module.
!
Complete the demonstrations and labs.
!
Read Module 5, “Configuring Network Security by Using Public Key
Infrastructure,” in Course 2153, Implementing a Microsoft Windows 2000
Network Infrastructure.
!
Read Module 6, “Configuring Network Security by Using IPSec,” in Course
2153, Implementing a Microsoft Windows 2000 Network Infrastructure.
!
Read Module 5, “Implementing Security on a Web Server,” in Course 2295,
Implementing and Supporting Microsoft Internet Information Services 5.0.
!
Read the article “Step-by-Step Guide to Internet Protocol Security (IPSec),”
which is available at http://www.microsoft.com/windows2000/techinfo/
planning/security/ipsecsteps.asp.
!
Read the TechNet article, “Authentication and Encryption,” which is
available at http://www.microsoft.com/technet/security/network/authen.asp.
!
Read the Microsoft MSDN
®
Magazine article, “Web Security: Putting a
Secure Front End on Your COM+ Distributed Applications,” which is
available at http://msdn.microsoft.com/msdnmag/issues/0600/
websecure/websecure.asp.
Presentation:
120 minutes
Lab:
30 minutes
Required materials
Preparation tasks
iv Module8:ProtectingCommunicationPrivacyandDataIntegrity
!
Read the MSDN article, “The Evolution of Security on the Web: An
Introduction to Cryptosystems on the Internet,” which is available at
http://msdn.microsoft.com/library/en-us/dnsecure/html/msdn_websec.asp.
!
Read the VeriSign article, “Implementing Web Site Client Authentication
Using Digital IDs,” which is available at http://www.verisign.com/
clientauth/kit/details.html.
!
Read the VeriSign article, “Guide to Securing Your Web Site For
Business,” which is available at http://www.verisign.com/resources/
gd/secureBusiness/secureBusiness.html.
Module8:ProtectingCommunicationPrivacyandDataIntegrity v
How to Teach This Module
Begin this module with a discussion of the types of attacks that are possible on
the communication link between the browser and the Web server.
Lesson: Introduction to Cryptography
It is an interesting sidebar to mention the role that cryptographic code breaking
played in World War II. “Enigma,” “Purple,” and “Magic” are the code names
of some of the more well-known cryptographic systems. You can find more
information about cryptography during wartime by searching for “cryptography
World War II” on the Internet.
Mention that symmetric encryption is very fast and that it is the most efficient
way to transfer larger quantities of data securely.
By using asymmetric encryption, the recipient of the encrypted data can be
assured that the data came from the owner of the public key. Therefore, not
only can asymmetric encryption be used to encrypt the data, it also provides a
guarantee of the data’s origin.
Note that the key length plays an important role in the strength of the
encryption. If the key length is long enough, it is virtually impossible to guess.
Storing private keys is the most challenging aspect of encryption. For more
information about this topic, direct students to the book, Writing Secure Code,
by Michael Howard and David LaBlanc (Redmond: Microsoft Press
®
), 2002.
An important distinction between encryption and hashing is that encryption
scrambles the data such that it can be unscrambled, whereas hashing cannot be
reversed.
You can sign data without hashing it to guarantee that the data came from you;
however, this would not guarantee that the data was not changed en route to the
recipient.
After reviewing the answers to the practice, brainstorm with the students for
more scenarios of when cryptography could be used in Web applications.
Lesson: Working with Digital Certificates
Mention briefly that one of the reasons for obtaining a certificate (personal or
server) is to use SSL to communicate with a Web server. Students will learn
more about the SSL/TLS and IPSec protocols later in this module.
You can do the steps of this practice with the students and show the
nwtraders.msft certificate, which is the certificate from the London CA.
Students may ask about the process that is required to become a CA, such as
VeriSign. Although anyone who uses Certificate Services can generate
certificates, not everyone who generates certificates is a trusted CA. Trust is
based on many factors, including the length of time that the CA is in business,
the CA’s reputation, and the process that the CA uses to verify those who
request certificates.
What Is Cryptography?
How Does Symmetric
Encr
y
ption Work?
How Does Asymmetric
Encryption Work?
Exchanging and Storing
Ke
y
s
Verifying DataIntegrity
with Hashes
Using Digital Signatures
Practice: Using
Cr
y
pto
g
raph
y
What Are Digital
Certificates?
Practice: Viewing Digital
Certificates
What Is a Certificate
Authorit
y
?
vi Module8:ProtectingCommunicationPrivacyandDataIntegrity
This animation provides an overview of the process of how certificates are
requested and granted from a CA, and then how those certificates are used to
communicate securely over SSL. You might consider postponing this animation
until the next lesson, which discusses SSL.
Note that the “random bits” referred to in the multimedia are the session key.
For certificates to be effective, they must be trusted. Certificate chains enable
users to trace a certificate back to the original CA.
If time permits, demonstrate the use of the Certificate Manager tool.
Discuss some of the reasons why a user would want to obtain a personal
certificate.
Note
The options for certificate templates offered by the Certificate Request
Wizard depend on how you installed the Microsoft Management Console
(MMC) Certificates snap-in:
!
If you installed the MMC Certificates snap-in to manage certificates for My
user account, as directed in the “Practice: Viewing Digital Certificates”
topic, you get Authenticated Session, Basic EFS, and User Signature
Only templates.
!
If you installed the MMC Certificates snap-in to manage certificates for
Computer account, you get Computer and IPSEC templates.
You will need to lead this practice and also get a personal certificate; make sure
to enter Research for your department, because this field will be used in the
client certificate mapping demonstration.
As the students submit their requests for personal certificates, you need to issue
the certificates. The issuing of certificates should be done with little explanation
and with the screen blanked so that the students do not get confused between
the request and issue processes.
!
To process the certificate requests with Microsoft Certificate Services
for Microsoft Windows
®
2000
1. On the Start menu, click Programs, click Administrative Tools, and then
click Certification Authority.
During setup, the instructor computer was set up with Certificate Services
and was created as a stand-alone root CA.
2. Expand the nwtraders.msft CA, and then click Pending Requests.
There will be one certificate request from each student.
3. To accept the request and issue a certificate, right-click the request, click All
Tasks, and then click Issue.
The request is moved from the Pending Requests node to the Issued
Certificates node.
Multimedia: Using
Digital Certificates
Certificate Chains and
Hierarchies
Certificate Stores
Obtaining a Personal
Certificate
Note
Instructor-Led Practice:
Obtaining a Personal
Certificate
Module8:ProtectingCommunicationPrivacyandDataIntegrity vii
Show how the SSL port, 443, is disabled by opening Internet Information
Services (IIS) and viewing the Web Site tab for the Mod08 folder of the
2300Demos Web application.
Explain to students that they will obtain a server certificate in the lab; therefore,
they can just watch the demonstration now, rather than performing the steps.
When processing the certificate request with Certification Services, do not
explain what is being done. This step occurs only because you are using
Certificate Services in the classroom.
Lab 8.1: Obtaining a Server Certificate
Both the TailspinToys and TailspinToysAdmin Web applications contain Web
pages that either request private information from users or deliver private
information to users. Before students can turn on SSL for these Web pages,
they need to obtain a server certificate for their Web servers.
Students will request the server certificates from the London CA. You will need
to approve the requests as they are made by the students.
!
To issue certificates by using Certificate Services
After students have submitted their requests for server certificates, you must
issue the certificates:
1. On the Start menu, click Programs, click Administrative Tools, and then
click Certification Authority.
2. Expand the nwtraders.msft CA, and then click Pending Requests.
There will be a certificate request from each student.
3. To accept a request and issue a certificate, right-click the request, click All
Tasks, and then click Issue.
The request is moved from the Pending Requests folder to the Issued
Certificates folder.
Lesson: Using the Secure Sockets Layer/Transport Layer Security
Protocols
Students may have heard of both SSL and TLS. It is important to note that TLS
is the most recent version of the protocol and that although SSL is the more
commonly referred-to protocol, it is most likely TLS that is being used.
Mention that SSL/TLS are the protocols that enable the secure communications
that are described in the animation “Using Digital Certificates.” You might
consider showing this animation here instead of in the previous lesson.
Mention the steps that are required before SSL can be enabled in IIS. You will
demonstrate the process of enabling SSL in the demonstration that follows this
topic.
Show how SSL is enabled in IIS. Discuss the various options that are available
for client certificates.
Obtaining a Server
Certificate
Demonstration:
Obtaining a Server
Certificate
Overview of Security
Protocols
How Does SSL/TLS
Work?
Enabling SSL for an IIS
Web Application
Demonstration:
Enabling SSL
viii Module8:ProtectingCommunicationPrivacyandDataIntegrity
Discuss both the Active Server Pages (ASP) method and the Microsoft
ASP.NET method of verifying the authenticity of client certificates.
Before students can view the pages in the practice, you must configure the
Mod08 folder of the 2300Demos Web application to require client certificates.
After students have accessed the WhoAmI.asp and ReadCertInfo.aspx pages in
the Mod08 folder of the 2300Demos Web application on the London computer,
examine the source code for the pages in Microsoft Visual Studio
®
.NET:
1. In Visual Studio .NET, open the WhoAmI.asp page in the Mod08 folder of
the 2300Demos project.
2. In Visual Studio .NET, open the ReadCertInfo.aspx page in the Mod08
folder of the 2300Demos project.
The page displays information from a client certificate by using the
HttpClientCertificate object.
Client certificate mapping is a powerful authentication method that allows IIS
to perform work on behalf of the client, based on the contents of a client
certificate. Emphasize IIS client certificate mapping. Information on
Active Directory
®
directory service mapping is provided for those students that
have previous experience with Active Directory.
Demonstrate how to enable many-to-one client certificate mapping in the
2300Demos Web application. Note that client certificate mapping is not used in
the labs.
SSL should be used only for those portions of the Web application that require
secure communications. There is a performance cost that is associated with
using SSL, and care should be taken to ensure that SSL is used only when
necessary. Discuss the guidelines for using SSL.
Run this practice as a group brainstorming session where students determine
which pages in the TailspinToys and TailspinToysAdmin Web applications
should be protected with SSL.
Lesson: Using Internet Protocol Security
Note that although IPSec is not commonly used for securing communications
between client computers and Web applications on the IIS Web server, IPSec
does have a role in protecting communications between the IIS Web server and
the other computers and resources that are on the organization’s network.
Briefly discuss the process of implementing IPSec.
Understanding how IPSec and SSL/TLS differ is important when deciding
where to apply each protocol. Discuss each difference between IPSec and
SSL/TLS.
Lab 8.2: ProtectingCommunicationPrivacyandDataIntegrity
In Lab 8.2, students will turn on SSL for portions of the TailspinToys and
TailspinToysAdmin Web applications.
Verifying the
Authenticity of Client
Certificates
Instructor-Led Practice:
Verifying the
Authenticity of Client
Certificates
Using Client Certificate
Mappin
g
Demonstration: Client
Certificate Mapping
Guidelines for Using
SSL/TLS
Practice: Requiring SSL
for Web Application
Pages
Overview of IPSec
Implementing IPSec
Comparing IPSec and
SSL/TLS
Module8:ProtectingCommunicationPrivacyandDataIntegrity ix
Customization Information
This section identifies the lab setup requirements for a moduleand the
configuration changes that occur on student computers during the labs. This
information is provided to assist you in replicating or customizing Microsoft
Official Curriculum (MOC) courseware.
Lab Setup
To complete this lab, the WebUser login and the InternetStoredProcs and
IntranetStoredProcs roles must be added to Microsoft SQL Server
™
on the
Glasgow computer.
!
Configure SQL Server on the Glasgow computer
• If you did not perform the “Adding Roles and Logins to SQL Server”
demonstration in Module 7, “Securing Microsoft SQL Server,” in Course
2300, Developing Secure Web Applications, you must do it now.
To complete this lab, students can continue working in the Tailspin Toys
Visual Studio .NET projects that they used in previous labs, or they can start
with new files.
To start with new files, students must complete the following steps.
!
Create the Web applications for the ASP exercises
1. Copy all of the contents of the ASP starter folder install_folder\Labfiles\
Lab08_2\ASP\Starter\TailspinToys to the TailspinToys IIS virtual directory
at C:\Inetpub\wwwroot\TailspinToys.
2. Copy all of the contents of the ASP starter folder install_folder\Labfiles\
Lab08_2\ASP\Starter\TailspinToysAdmin to the TailspinToys IIS virtual
directory at C:\Inetpub\wwwroot\TailspinToysAdmin.
!
Create the Web applications for the ASP.NET exercises
1. Copy all of the contents of the ASP.NET folder install_folder\Labfiles\
Lab08_2\ASPXVB\Starter\TailspinToys.NET to the TailspinToys.NET IIS
virtual directory at C:\Inetpub\wwwroot\TailspinToys.NET.
2. Copy all of the contents of the ASP.NET folder install_folder\Labfiles\
Lab08_2\ASPXVB\Starter\TailspinToysAdmin.NET to the
TailspinToysAdmin.NET IIS virtual directory at C:\Inetpub\wwwroot\
TailspinToysAdmin.NET.
3. Edit the file c:\Inetpub\wwwroot\TailspinToysAdmin.NET\Web.config and
change the <allow roles="London\TailspinAdmins"/> tag to be <allow
roles="machineName\TailspinAdmins"/>, where machineName is the name
of your computer.
x Module8:ProtectingCommunicationPrivacyandDataIntegrity
!
Configure IIS authentication
1. Run the IIS administrative tool.
2. Expand the computer node and the Default Web Site node in the tree.
3. Right-click the TailspinToysAdmin virtual directory, and then click
Properties.
4. Click Directory Security.
5. In the Anonymous access and authentication control group, click Edit.
6. Clear the Anonymous access check box.
7. Click OK twice to save your changes.
8. Right-click the TailspinToysAdmin.NET virtual directory, and then click
Properties.
9. Click Directory Security.
10. In the Anonymous access and authentication control group, click Edit.
11. Clear the Anonymous access check box.
12. Click OK twice to save your changes.
Lab Results
Performing the labs in this module introduces the following configuration
changes:
!
The Login.asp and ChangePassword.asp pages are moved into a private
folder in the TailspinToys Web application.
!
The Login.aspx and ChangePassword.aspx pages are moved into a private
folder in the TailspinToys.NET Web application.
!
The private folder in each of the following Web applications is configured
in IIS to require SSL:
• TailspinToys
• TailspinToys.NET
• TailspinToysAdmin
• TailspinToysAdmin.NET
[...]... Howard and David LaBlanc (Redmond: Microsoft Press), 2001 Module 8:ProtectingCommunicationPrivacyandDataIntegrity 11 Verifying DataIntegrity with Hashes User B User A DataData Hash value Hash value Hash algorithm Hash algorithm DataData Hash algorithm Hash algorithm DataData Hash value Hash value If hash If hash values values match, match, data is valid data is valid Hash value Hash value Data. .. hashing and digital signing 4 Module8:ProtectingCommunicationPrivacyandDataIntegrity What Is Cryptography? ! Cryptography is the science of protectingdata " Protects a user's identity or data from being read " Protects data from being altered " Verifies that data originates from a particular user ! Encryption is the process of scrambling data ! Encryption is only as strong as the key Data Data... actively monitor, capture, and control the data that passes between two communicating computers without the knowledge of the affected parties (for example, the attacker can reroute a data exchange) Note The code samples in this module are provided in both Microsoft® Visual Basic® NET and C# 2 Module8:ProtectingCommunicationPrivacyandDataIntegrity Objectives After completing this module, you will be... the password 12 Module8:ProtectingCommunicationPrivacyandDataIntegrity Using Digital Signatures User A User B DataDataDataData Hash algorithm Hash algorithm Hash algorithm Hash algorithm User B User B User B User B Hash value Hash value Hash value Hash value Private key 1 2 2 3 Private Public key Hash value Hash value If hash values If hash values match, data came match, data came from the... connection between a client application and a server application (such as a Web browser and Web server) ! Secure Multipurpose Internet Mail Extensions (S/MIME) A protocol that is used for sending secure e-mail ! IPSec A computer-to-computer protocol that supports privacy, authentication, anddataintegrity 18 Module8:ProtectingCommunicationPrivacyandDataIntegrity Practice: Viewing Digital Certificates... message or other forms of communication to obtain the keys Note For more information about encryption algorithms, see the topic “Supported Algorithms” in the Microsoft MSDN® online documentation 5 6 Module8:ProtectingCommunicationPrivacyandDataIntegrity How Does Symmetric Encryption Work? ! Same encryption algorithm and key are used to both encrypt and decrypt the data ! Fast and efficient ! Difficult... 14 Module8:ProtectingCommunicationPrivacyandDataIntegrity 4 You want to send data to a user and have the user be sure that the file is from you and has not been changed en route Create a hash of the file and sign the hash to send along with the file 5 You want to send a broadcast message with important data You do not... difficult and time consuming, if not impossible, for an attacker to decipher the data Encryption is often used in the following types of transactions: ! E-mail ! E-commerce ! File storage ! Database connections ! Web client authentication Module8:ProtectingCommunicationPrivacyandDataIntegrity How is data encrypted? An encryption algorithm, also called a cipher, is used with secret data, which... Add Standalone Snap-in dialog box, and then in the Add/Remove Snap-in dialog box, click OK ! View certificates on your computer 1 In Microsoft Management Console (MMC), expand the Certificates node, which is under the Console Root node 2 Expand the Personal node Do you have any personal certificates installed? No Module8:ProtectingCommunicationPrivacyandData Integrity. .. http://msdn.microsoft.com/library/default.asp?url=/library/en-us/dnmag01/ html/com0105.asp 10 Module8:ProtectingCommunicationPrivacyandDataIntegrity If your process runs as SYSTEM (such as an Active Server Pages (ASP) page), you can store keys in the Local Security Authority (LSA) by using LsaStorePrivateData and LsaRetrievePrivateData LSA can store only a fixed (small) number of keys, however, so this option .
Lab 8.2: Protecting Communication
Privacy and Data Integrity 65
Course Evaluation 76
Module 8: Protecting
Communication Privacy
and Data Integrity.
gd/secureBusiness/secureBusiness.html.
Module 8: Protecting Communication Privacy and Data Integrity v
How to Teach This Module
Begin this module with a discussion