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FAQs

  • Q. How can I verify that my Windows Server 2003 Certificate Authority (CA) deployment is correctly configured?
  • Q. How do I enable HTTP Secure (HTTPS) traffic on my Microsoft Internet Information Systems (IIS) 6.0 Web server site by using my local forest Certificate Authority
  • Q. How can I enable digital certificate autoenrollment in Windows Server 2003?
  • Q. How can I configure Microsoft Office Outlook 2003 for digital signatures and encryption?
  • Q. How can I export and import my private keys from one machine to another?

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FAQs

Q. How can I verify that my Windows Server 2003 Certificate Authority (CA) deployment is correctly configured?

A. Microsoft provides the PKI Health Tool (PKView.exe) as part of the Windows 2003 Resource Kit Tools (http://www.microsoft.com/downloads/details.aspx?familyid=9d467a69-57ff-4ae7-96ee-b18c4790cffd&displaylang=en). PKView determines whether the Authority Information Access (AIA) and Certificate Revocation List (CRL) distribution point URLs are valid and reachable. The tool also determines whether the associated certificates are nearing expiration. To run PKIView, select Start, Run, and type pkiview.msc A Microsoft Management Console (MMC) instance will initiate. Select a CA to display the status of each CRL and AIA location, as Figure 1 shows. If you have more than one CA in your hierarchy, select each CA in turn to check the status of the whole hierarchy. The status field should display OK for all entries. If the publication point isn't correctly configured or the CA certificate or CRL isn't copied correctly to the publication point (i.e., missing), the status will show "Unable to Download." If the CA certificate or CRL is nearing expiration, the status column will display "Expiring."

Q. How do I enable HTTP Secure (HTTPS) traffic on my Microsoft Internet Information Systems (IIS) 6.0 Web server site by using my local forest Certificate Authority (CA)?

A. If you have Certificate Services installed in your Active Directory (AD) forest, enabling HTTPS traffic on a Web server is a simple exercise. To do so, perform these steps:

  1. Log on to the Web server as an account with local Administrator privileges (to allow certificates to be installed into the computer's local certificate store).
  2. Start the Internet Information Services Manager (Start, Programs, Administrative Tools, Internet Information Services--IIS--Manager).
  3. Expand Web Sites and right-click the Web site for which you want to enable HTTPS communication (e.g., Default Web Site) and select Properties.
  4. Select the Directory Security tab and click Server Certificate, as Figure 2shows.
  5. Click Next on the "Welcome to the Web Server Certificate Wizard" page.
  6. Select "Create a new certificate" and click Next.
  7. You now choose whether to immediately request the certificate or prepare a request to be submitted later. If the CA is correctly configured in the AD forest, select the "Send the request immediately to an online certificate authority." Click Next.
  8. Enter a name for the certificate (e.g., Exchange Web Server SSL), as Figure 3 shows. Leave the default values for bit length and cryptographic service provider (CSP). Click Next.
  9. Enter the organization's name and unit (e.g., SavillTech and IT) and click Next.
  10. Enter the common name (CN) of the certificate. This name must be the full name of how users will access the Web site (e.g., savdalex01.savilltech.com) and click Next.
  11. Enter the Country, State, and City and click Next.
  12. You'll be prompted for the port to be used for Secure Sockets Layer (SSL). Leave it as the default (443) and click Next.
  13. You'll see a list of CAs known to AD. Select one and click Next.
  14. You'll see a confirmation of the certificate request. Click Next.
  15. The screen displays a success message. Click Finish. After you install the certificate, Web clients will be able use HTTPS.

If you have concerns with this approach, you can use the Web-based enrollment method. (I know of people who were unable to get this auto enrollment process to work. Usually this occurs because firewall or server-side configuration issues on the certificate server prevent remote procedure call (RPC) from being available):

  1. Log on to the IIS server.
  2. Go to http:///certsrv/ .
  3. Click "Request a certificate."
  4. Click "Advanced certificate request."
  5. Click "Create and submit a request to this CA."
  6. Complete the Certificate Template form, ensuring that the Certificate Template is set to Web Server and the "Store certificate in the local computer certificate store" check box is selected, as Figure 4 shows. The Name field needs to match how the clients will connect to the server (the server part of the URL).
  7. Click Submit.
  8. Click Yes to the security warning.
  9. You'll see a new Web page. Select "Install this certificate" and click Yes to the security warning.
  10. You'll see a message saying the certificate was successfully installed

You can now click the Server Certificate button under the Directory Security of the Web site, then select "Assign an existing certificate" and select the installed certificate.

Q. How can I enable digital certificate autoenrollment in Windows Server 2003?

A. Autoenrollment is available to Windows 2003 and Windows XP domain members for version 2 certificate templates (which can be issued only by enterprise certificate authorities--CAs--running Windows 2003 Enterprise or Datacenter Edition). The autoenrollment process grants certificates based on certificate templates that are supplied with Read, Enroll, and Autoenroll permissions for the users, groups, or computers who require autoenrollment. A modification is made to Group Policy to initiate the process during a Group Policy refresh or interactive logon event. Make sure that the certificate templates to be configured for autoenrollment don't require user input because if they do, the autoenroll process will fail. In this example, we'll enable autoenrollment for certificates to be used for digital signatures and message encryption via Microsoft Office Outlook 2003:

  1. Start the Microsoft Management Console (MMC) Certificate Authority (CA) snap-in (Start, Programs, Administrative Tools, Certification Authority).
  2. Expand the CA server and right-click Certificate Templates. Select Manage from the displayed context menu.
  3. Right-click the Exchange Signature Only template and select Duplicate Template from the menu.
  4. Select the General tab and enter a name for the new template (e.g., Exchange Signature Only Custom). Don't enable digital signature publishing in AD (this is not needed for signatures because the certificate is enabled in the payload of the message sent).
  5. Under the Request Handling tab, set the purpose to Signature. Select "Enroll subject without requiring any user input" and select the "Allow private key to be exported" check box, as Figure 5shows. Alternatively, if you have archiving enabled, you can select the "Archive subject's encryption private key" (the option might be grayed out depending on the type of certificate you're duplicating). It's advisable to enable the key archival in case a private key is lost)
  6. Click the Subject Name tab and select "Build from this Active Directory information." Set "Subject name format" to "Fully distinguished name" and select the "Include e-mail name in subject name" check box.
  7. Select the Security tab and ensure that Read, Enroll, and Autoenroll are enabled for the users (e.g., Domain Users) who will autoenroll as Figure 6 shows. Some companies have a process whereby users are added to a group if they require certain certificate autoenrollments, which then are processed on their next logon or Group Policy refresh. Click OK.
  8. Repeat the above steps for Exchange User, except that under the General tab, you need to enable publishing to the AD (this results in the public certificate being placed in the user's userCertificate attribute for the user and is queried via the global catalog (GC) by the sending party and will be visible under the "Published Certificates" tab for the user in the Active Directory Users and Computers MMC snap-in). Also, under Request Handling, set the Purpose to Encryption.
  9. Close the Manage templates snap-in.
  10. Under Certificate Templates within the Certification Authority snap-in, right-click and select "New - Certificate Template to Issue." 11. Select a certificate that you want to issue and click OK, as Figure 7 shows. (Certificates that are already being issued aren't shown in the dialog box). Repeat this process for the certificates you just created (e.g., Exchange User Custom and Exchange Signature Only Custom.

Make sure you choose the copied template that you created and not the original (i.e., select Exchange User Custom, not Exchange User). The original template doesn't permit autoenroll. Next you need to enable the Group Policy for the autoenrollment. To do so, perform these steps:

  1. Open the GPO that applies to the container (e.g., domain or OU that will affect the users/computer requiring autoenrollment) or create a new GPO. (For example, open the MMC Active Directory Users and Computers snap-in, right-click the container, and select Properties. Select the Group Policy tab, select the GPO and click Edit, as Figure 8 shows.)
  2. Under the GPO's Computer Configuration and User Configuration main branches, expand Windows Settings, Security Settings, Public Key Policies and double-click the Autoenrollment Settings. (You want to set this at both computer and user level.)
  3. Enable the "Enroll certificates automatically" and select the two check boxes for renewing expired certificates and updating certificates that use certificate templates, as Figure 9 shows. Click OK
  4. Close the GPO editor.

When users next logon or have Group Policy applied, they should receive the certificates within 90 seconds. You can verify that users received the certificates by performing these steps:

  1. Start the MMC console (Start, Run, MMC).
  2. From the File menu, select Add/Remove Snap-in.
  3. Click Add from the Standalone tab of the Add/Remove snap-in dialog box.
  4. Select Certificates, click Add, then click Close, as Figure 10 shows.
  5. Click OK to the main Add/Remove Snap-in dialog. You'll now see the certificates under Certificates, Current User, as Figure 11 shows.

You can check the Application event log for information related to autoenrollment on the client. (You can also view Failed Requests in the Certificate Authority MMC snap-in.) Figure 12 shows a failed autoenrollment from the client Application event log.

The failed autoenrollment occurred because the remote procedure call (RPC) server wasn't available on the CA that was running on Windows Server 2003 Enterprise Edition with Service Pack 1 (SP1) installed. Because the CA was enabled on the server after the Security Configuration Wizard (SCW) had been run, the services and ports needed by certificate servers weren't enabled. To resolve the problem, run the SCW (Start, Programs, Administrative Tools, Security Configuration Wizard) and enable the Certificate Server in the Select Server Roles section and the "Ports used by System RPC applications" option in the "Open Ports and Approve Applications" section.

To view the certificates that have been issued from a certificate server, expand the Issued Certificates branch of the Certification Authority MMC snap-in, as Figure 13 shows.

Be careful when using autoenrollment for the Exchange User certificate, which is used to encrypt messages when users log on to more than one machine and access mail. Messages are encrypted with a generated symmetric key (i.e., the key is used to both encrypt and decrypt the message) and the symmetric key is transmitted with the message encrypted with the recipient's public key. This means that only the recipient's private key can decrypt the symmetric key and thus decrypt the message.

The problem is that if you use autoenrollment and a user logs on to multiple machines, each machine will generate a new set of private and public keys for that user (because a separate profile is used on each machine). Thus, depending on which public key is used to encrypt a message, the recipient will be able to open the message only on the computer with the paired private key. On all other machines the corresponding private key is missing and the message is unreadable.

The solution is to store these certificates (private keys) on smart cards that travel with the user instead of on the machines or use roaming profiles so that the user always has the same profile and thus no additional certificate enrollments will take place.

With Windows 2003 and Windows Vista, Digital Identity Management Service (DIMS) enables credential roaming, in which the certificates and private keys are stored in AD, avoiding the problem. You can find more information about this problem at http://technet2.microsoft.com/WindowsServer/en/Library/d052e2b5-fd73-4bd0-8018-7713049463ee1033.mspx.

Q. How can I configure Microsoft Office Outlook 2003 for digital signatures and encryption?

A After a user has the certificates required for digital signatures and encryption installed, enabling them in Outlook is relatively simple. To do so, perform these steps:

  1. Open Outlook and Select Options from the Tools menu.
  2. Select the Security tab and click Settings.
  3. If you're prompted to "Get a Digital ID," you don't have certificates. Otherwise, the dialog box will show "My S/MIME Settings ()" as the Security Settings Name, and S/MIME as the Cryptography Format, as Figure 14 shows.
  4. Click OK.

When an Outlook user sends email, the client displays two buttons that enable digital signing and encryption of messages, as Figure 15 shows.

When a user receives a digitally signed message, the user will see a padlock and ribbon icon above the message body. You can view the signature validation by clicking the ribbon icon, as Figure 16 shows.

To enable encrypted messages to be sent, both sender and recipients need each others' public keys, so a digitally signed message must have been sent in advance and a reply sent from the recipient (which shares the public keys). If keys are published in Active Directory (AD), you can send encrypted messages to a recipient with no prior communication. If you don't have access to the recipient's public key, you'll receive an error message stating which recipients had missing or invalid certificates.

You might also see the error message if you're using Outlook 2003 in cached mode and you're trying to mail someone who only recently acquired public key infrastructure (PKI) services (within the past 24 hours). Outlook 2003 cached mode queries the Offline Address Book (OAB), which it only downloads every 24 hours. If you know the recipient does have a certificate, force a download of the latest copy of the OAB (Tools, Send/Receive, Download Address Book). You might also need to force a rebuild of the OAB on the Exchange server (which by default is updated each day at 4 A.M.) To force a rebuild, open Exchange System Manager (ESM), select Recipients, Offline Address Lists. Right-click Default Offline Address List and select Rebuild. You should perform this rebuild before downloading the OAB from the Outlook client.

As with digital signatures, if a message is encrypted, a padlock icon appears on the message header. Click the icon to display more information, as Figure 17 shows.

Q. How can I export and import my private keys from one machine to another?

A. By default, private keys are stored in the requesting user's or computer's certificate store. If you use multiple machines, you might want your private key on multiple machines. To do so, perform these steps:

  1. Start the Microsoft Management Console (MMC) (Start, Run, MMC).
  2. From the File menu, select Add/Remove Snap-in.
  3. Select the Standalone tab and Click Add.
  4. Select Certificates and click Add. Click Close.
  5. Click OK to the main Add/Remove Snap-in dialog box.
  6. Select Certificates, Current User, Personal, Certificates.
  7. In the right pane, right-click the certificate you want to export (e.g., Exchange User) and select All Tasks, Export, from the context menu.
  8. Click Next to the Export Wizard welcome dialog box.
  9. Select "Yes, export the private key" and click Next.
  10. Leave the default export options and click Next.
  11. Enter a password for the export and click Next.
  12. Enter a location and name for the exported key and click Next.
  13. Click Finish in the summary dialog box.
  14. Click OK to the export confirmation dialog box.

Copy the export key file to another machine and perform the following steps to import the key:

  1. Start the MMC console.
  2. From the File menu, select the Add/Remove snap-in.
  3. Select the Standalone tab and click Add.
  4. Select Certificates and click Add, then click Close.
  5. Click OK to the main Add/Remove Snap-in dialog box.
  6. Select Certificates, Current User, Personal, Certificates.
  7. Right-click Certificates and select Import from the context menu.
  8. Click Next at the Import Wizard welcome screen.
  9. Enter the name of the file to import, as Figure 18 shows, and click Next.
  10. Enter the password for the export file and, optionally, select the check box to enable the key to be exportable again in the future. Click Next.
  11. Select the option to store the certificate in the default Personal store and click Next.
  12. Click Finish to complete the import.
  13. Click OK to the import confirmation message. After the import is complete, encrypted messages will be readable on the additional machine.
By default, private keys are stored in the requesting user's or computer's certificate store. If you use multiple machines, you might want your private key on multiple machines. To do so, perform these steps:

  1. Start the Microsoft Management Console (MMC) (Start, Run, MMC).
  2. From the File menu, select Add/Remove Snap-in.
  3. Select the Standalone tab and Click Add.
  4. Select Certificates and click Add. Click Close.
  5. Click OK to the main Add/Remove Snap-in dialog box.
  6. Select Certificates, Current User, Personal, Certificates.
  7. In the right pane, right-click the certificate you want to export (e.g., Exchange User) and select All Tasks, Export, from the context menu.
  8. Click Next to the Export Wizard welcome dialog box.
  9. Select "Yes, export the private key" and click Next.
  10. Leave the default export options and click Next.
  11. Enter a password for the export and click Next.
  12. Enter a location and name for the exported key and click Next.
  13. Click Finish in the summary dialog box.
  14. Click OK to the export confirmation dialog box.

Copy the export key file to another machine and perform the following steps to import the key:

  1. Start the MMC console.
  2. From the File menu, select the Add/Remove snap-in.
  3. Select the Standalone tab and click Add.
  4. Select Certificates and click Add, then click Close.
  5. Click OK to the main Add/Remove Snap-in dialog box.
  6. Select Certificates, Current User, Personal, Certificates.
  7. Right-click Certificates and select Import from the context menu.
  8. Click Next at the Import Wizard welcome screen.
  9. Enter the name of the file to import, as Figure 18 shows, and click Next.
  10. Enter the password for the export file and, optionally, select the check box to enable the key to be exportable again in the future. Click Next.
  11. Select the option to store the certificate in the default Personal store and click Next.
  12. Click Finish to complete the import.
  13. Click OK to the import confirmation message. After the import is complete, encrypted messages will be readable on the additional machine.

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