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If you plan to implement client certificates, ensure that you have an efficient process in place for issuing and managing client certificates. Each client certificate must be stored on the client computer or on a device like a smart card. In large organizations with thousands of client computers, distributing and managing the client certificates can be a great deal of work. However, client certificates do provide an extra level of security if you have a Web site that requires a very high level of security.
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The most important decision that you need to make when obtaining the server certificates is deciding from where you will get the certificates. You have essentially two choices: you can obtain server certificates from a commercial CA, or you can deploy a CA inside your organization and use it to issue the server certificates. Both Microsoft Windows 2000 Server and Microsoft Windows Server 2003 include a Certificate Services component that you can use to create a CA. Creating your own CA and using it to issue the server certificates has a couple of advantages. First, if you use the Certificate Services included with Windows Server, you do not have to pay for the Certificate Server software or any of the certificates. Second, if you install your own CA, you have complete control of issuing and managing the certificates.
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Security Alert If you do decide to deploy your own CA infrastructure, you need to ensure that your CA infrastructure is very secure. If an attacker can ever compromise your root CA, or obtain a subordinate CA certificate from the root CA, every certificate issued by the CA becomes suspect. If this happens, you will need to rebuild your entire CA infrastructure and reissue all client certificates.
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Despite these advantages, however, you probably should not use your own CA to issue certificates for your ISA Server or public Web server. This is especially true if users from outside your organization will be accessing the Web site. The reason for this is that the client software will not be configured to trust your internal CA and the users will get an error message every time they access your Web site. PKI is built on the concept of trust; when a client computer connects to a Web server, the client checks to see if it trusts the CA that issued the server certificate. If the client is configured to trust the CA, then the SSL negotiation begins. If the client is not configured to trust the CA, the user will receive an error message, or the connection will fail. Most Web browsers are preconfigured with certificates for the most popular commercial CAs.
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Using an Enterprise CA installed on Windows Server 2003 or Windows 2000 Server can greatly simplify the process of managing certificates. The Enterprise CA requires, and is tightly integrated with Active Directory. You can configure policies in Active Directory that automate the process of issuing and renewing certificates. Moreover, certificates issued to domain users are stored in Active Directory so the public keys can easily be retrieved by other clients. If you are running Active Directory, and only internal clients will connect to your ISA Server or Web servers, an Enterprise CA can greatly simplify your certificate management processes.
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How to Install Digital Certificates on ISA Server
Once you have decided where you will get the certificate from, the next step is obtaining and installing the server certificate on ISA Server. Depending on the required configuration, you may also need to install a certificate on the internal Web server. The procedure for installing a server certificate on the computer running ISA Server varies depending on the CA you are using and on the ISA Server computer configuration, as follows:
If you use an internal CA that provides a Web site for clients to obtain certificates, you can connect to the Web site from the ISA Server computer and apply for and install the certificate. You will complete this procedure in the practice that follows this lesson. If you use an external CA, you need to create a certificate request and forward it to the external CA. You can create the certificate request on the server running ISA Server. However, this requires that IIS be installed on the computer running ISA Server. This is not recommended, so you should prepare the request on the Web server computer, install the certificate on the Web server computer, and then export it and import it to the ISA Server computer.
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