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System Center Configuration Manager 2007 : PKI Management References (part 2) - How SSL Works, Establishing a PKI

10/14/2013 9:02:32 PM
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2. How SSL Works

Both SSL (Secure Sockets Layer) and TLS (Transport Layer Security), which is replacing SSL, are cryptographic protocols providing security and data integrity for communications over TCP/IP (Transmission Control Protocol/Internet Protocol). SSL encrypts the segments of the Transport layer protocol, which is Layer 4 of the Open Systems Interconnection (OSI) model. An SSL client and server negotiate a stateful connection by using a handshaking procedure. During this handshake, the client and server agree on various parameters used to establish the connection’s security:

  • The initiation of the secure session begins when a client connects to an SSL-enabled server requesting a secure connection.

  • The server then picks the strongest cipher and hash function that it supports, and notifies the client of the decision.

  • The server sends back its identification in the form of a digital certificate, which contains the server name, the trusted Certificate Authority, and the server’s public encryption key.

The client may contact the server that issued the certificate (the trusted CA, as before) and confirm the certificate is authentic before proceeding:

  • In order to generate the session keys used for the secure connection, the client encrypts a random number with the server’s public key, and sends the result to the server. Only the server can decrypt it (with its private key). This is the one fact that makes the keys hidden from third parties, because only the server and the client have access to this data.

  • From the random number, both parties generate key material for encryption and decryption.

This concludes the handshake and begins the secured connection, which is encrypted and decrypted with the key material until the connection closes. If any one of the preceding processes fails, the SSL handshake fails and the connection is not created.

TLS and SSL have a variety of security measures:

  • The client may use the Certificate Authority’s public key to validate the CA’s digital signature on the server certificate. If the digital signature can be verified, the client accepts the server certificate as a valid certificate issued by a trusted CA.

  • The client verifies that the issuing CA is on its list of trusted CAs.

  • The client checks the server’s certificate validity period. The authentication process stops if the current date and time fall outside of the validity period.

  • Protection is provided against a downgrade of the protocol to a previous (less secure) version or a weaker cipher suite.

  • All the application records are numbered with a sequence number. Using this sequence number in the message authentication codes (MACs) provides additional security.

  • The message digest is enhanced with a key, so only a key holder can check the MAC, as specified in RFC 2104. (TLS only.)

  • The message that ends the handshake (Finished) sends a hash of all the exchanged handshake messages seen by both parties.

  • The pseudorandom function splits the input data in half and processes each one with a different hashing algorithm (MD5 and SHA1). It then XORs them together to create the MAC. This provides protection even if one of these algorithms is found vulnerable. (TLS only.)

  • SSL v3 improved upon SSL v2 by adding SHA1-based ciphers and support for certificate authentication. Additional improvements in SSL v3 include better handshake protocol flow and increased resistance to man-in-the-middle attacks.

3. Establishing a PKI

Microsoft provides native support for PKI in Windows Server 2003 and 2008 Active Directory. If you are running Windows 2000 Active Directory, special considerations are necessary because you must upgrade the schema to the Windows Server 2003 schema. This requires Windows 2000 domain controllers to be on SP 3 at a minimum.

With Microsoft Windows 2003 or 2008 Active Directory, the only configuration required for an Enterprise CA is if you have an Active Directory forest with multiple domains. In this scenario, you must add the CA’s computer account to each domain’s built-in Cert Publishers local group.

Configuration Manager Certificate Requirements

There are multiple certificate requirements for ConfigMgr to leverage PKI. If you already have a PKI in place in the organization, you must verify it meets the ConfigMgr requirements:

  • The PKI Root CA is running on the Enterprise or Datacenter edition of Windows Server 2003 or 2008.

  • Systems in any domain in the forest can recognize the Root CA as being trusted.

  • The site servers, site systems, computers, and devices must all have a certificate from the CA.

  • Certificates for the site servers, site systems, computers, and devices must reside in the personal store in the computer certificate store.

  • Clients must have a copy before they can accept the policies from the management point that is signed with this certificate.

  • Primary site servers cannot support key lengths greater than 8,096 bits.

  • Site systems do not have a published maximum key length.

  • Both computers and mobile device clients cannot support key lengths greater than 2,048 bits.

Caution: Encryption Key Length

Older network components used to have issues handling 2,048-bit (and higher) encrypted traffic. Although this is no longer an issue with today’s hardware, issues may still arise with some technologies. With IBCM being a focus of certificate usage, unknown home and Internet service provider (ISP) networks will need to support whatever key length you choose. Validate the bit length you are using will traverse all network mediums in your environment before rolling out to all systems.


If your organization does not have a PKI, it must determine what the architecture for the CA will look like, how many tiers it will have, what security measures will be put in place, the types of certificates it will issue, and whether the CA is published via AD or through a website. Microsoft provides valuable systematic guides for deploying certificates in the following environments:

  • Windows Server 2003— http://technet.microsoft.com/en-us/library/bb694035.aspx

  • Windows Server 2008— http://technet.microsoft.com/en-us/library/cc872789.aspx

When establishing a CA, it is best to use Windows Enterprise edition due to its advanced features not available in other versions of the OS. The issuance of version 2 certificate templates, private key archival, and role separation enforcement are only available when Certificate Services is installed on Windows Enterprise edition or Datacenter edition, the latter not being cost effective in most cases. You will need to issue certificates based off modified version 2 templates.

To install Certificate Services, execute the following steps on Windows Server 2003. Log on as a member of the Enterprise Admins security group with local Administrator rights on the server where the install is being performed. Then follow these steps:

1.
From the Start menu, select Control Panel and then click Add or Remove Programs.

2.
In the Add or Remove Programs window, click Add/Remove Windows Components.

3.
Scroll down and check the Certificate Services box.

4.
You also want to check the Application Server box, because this will open the details selection for that component. Verify that IIS (Internet Information Services) is selected and then click OK.

5.
In the Microsoft Certificate Services dialog box, click Yes to the warning about not changing domain membership after Certificate Services is installed.

6.
Click the Certificate Services Web Enrollment Support subcomponent.

7.
Click OK and then click Next.

8.
On the CA Type page, click Enterprise Root CA, check the Use Custom Settings to Generate the Key Pair and CA Certificate box, and then click Next.

9.
On the Public and Private Key Pair page, set the following options:

  • CSP— Microsoft Strong Cryptographic Service Provider

  • Allow the CSP to interact with the desktop— Disabled

  • Hash algorithm— SHA-1

  • Key length— 2,048

10.
On the Public and Private Key Pair page, click Next.

11.
On the CA Identifying Information page, enter the following information:

  • Common Name for this CA— ServerName

  • Distinguished name suffix— DC=mydomain,DC=com

  • Validity Period— 5 Years

12.
On the CA Identifying Information page, click Next.

13.
On the Certificate Database Settings page, accept the default settings and click Next.

14.
Click Yes on the Microsoft Certificate Services dialog box informing you Active Server Pages must be enabled on IIS if you wish to use the Certificate Services Web enrollment site.

15.
In the Microsoft Certificate Services dialog box, click Yes to create the necessary folders.

16.
If prompted, insert the Windows Server 2003 Enterprise Edition CD in the CD-ROM drive and choose the \i386 folder.

If prompted to insert the CD for the i386 folder, ensure you reapply whatever service pack the OS is running after installing Certificate Services.

17.
If prompted with a dialog box informing you Internet Information Services must be temporarily stopped, click Yes.

18.
On the Completing the Windows Components Wizard page, click Finish.

To install Certificate Services, execute the following steps on Windows Server 2008. You must be logged on as a member of the Enterprise Admins security group with local Administrator rights on the server where the install is being performed.

1.
Open Server Manager, click Add Roles, and click Next.

2.
Click Active Directory Certificate Services and then click Next two times.

3.
On the Select Role Services page, click Certification Authority and then click Next.

4.
On the Specify Setup Type page, click Enterprise and then click Next.

5.
On the Specify CA Type page, click Subordinate CA and then click Next.

6.
On the Set Up Private Key page, click Create a new private key. Click Next.

7.
On the Configure Cryptography page, select a cryptographic service provider, key length, and hash algorithm. Click Next.

8.
On the Request Certificate page, browse to locate the root CA (if the root CA is not connected to the network, save the certificate request to a file so that it can be processed later). Click Next.

9.
On the Configure CA Name page, create a unique name to identify the CA. Click Next.

10.
On the Set Validity Period page, specify the number of years or months that the CA certificate will be valid. Click Next.

11.
On the Configure Certificate Database page, accept the default locations or specify a custom location for the certificate database and certificate database log. Click Next.

12.
On the Confirm Installation Options page, review all the configuration settings you have selected. If you want to accept these options, click Install and wait until the setup process has finished.

Deploying PKI for ConfigMgr Native Mode

If you are deploying PKI for native mode, verify the following items:

1.
Confirm your PKI can support the various certificates required by Configuration Manager 2007 .

2.
Ensure the following computers in the Configuration Manager 2007 site have a trusted root Certificate Authority in common and intermediate Certificate Authorities as needed:

  • The site server

  • Management points (the default management point, proxy management point, Internet-based management point, and network load balanced management points)

  • Distribution points

  • Software update points

  • State migration points

  • All client computers and mobile client devices

3.
If you will use a Certificate Revocation List (CRL), publish it where all computers can locate it.

4.
Deploy the site server signing certificate to the site server, and determine how clients will retrieve it.

5.
Deploy the web server certificates to the following site systems and then configure IIS with the certificates:

  • Management points (the default management point, proxy management point, Internet-based management point, and network load balanced management points)

  • Distribution points

  • Software update points

  • State migration points

6.
This step is optional but recommended. On the site systems with the deployed web server certificates, create or modify a Certificate Trust List (CTL) in IIS to contain the root Certificate Authorities used by clients.

7.
Deploy client certificates to clients and management points.

8.
If you have mobile client devices, deploy the client device certificates.

9.
If you are using the Operating System Deployment feature, perform the following tasks:

  • Export root CA certificates that operating system clients will use during the deployment process so these can be imported into the Configuration Management console as a site setting.

  • Prepare and export one or more client certificates into a PKCS #12 file so that these can be included in the operating system deployment.

 
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