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The business of deciding which and how many certificates should be deployed can be complex . Here are a number of suggestions to guide the process:
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Minimize the number of certificates in use: The more certificates you use, the more it will cost for their purchase and the more complex the environment becomes . Use SAN certificates: Normal certificates contain a single name, but SAN certificates have multiple Subject Alternate Names (SAN), each one of which is a hostname . These are simpler to deploy and reduce the number of required
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certificates . For example, a SAN certificate might contain SANs for autodiscover . contoso .com, mail .contoso .com, hq-exserver3 .contoso .com, and exserver3, thus making that single certificate useful for a variety of purposes . Note that the FDQNs for RCA arrays do not need to be included in certificates, because these names are not used for SSL connections .
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Don t list individual computer hostnames in certificates: Whenever possible, use the names of arrays for Internet and intranet access to services (such as A ctiveSync), because these are flexible and expandable .
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In 5, Exchange Management Console and Control Panel, we discuss the New Certificate Wizard available in EMC. This is new for Exchange 2010 and it greatly simplifies the process of generating a request to a commercial trusted CA to allow it to issue an SSL certificate that meets your needs to secure whatever services you want to secure. The New-ExchangeCertificate cmdlet allows you to create a request for a certificate that you can send to your preferred certificate vendor. For example, this command creates a request for a SAN certificate that covers three hostnames:
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New-ExchangeCertificate GenerateRequest Path 'C:\Temp\Cert.req' SubjectName 'c=US;O=Contoso ;CN=Mail.contoso.com' DomainName 'mail.contoso.com, autodiscover.contoso.com, legacy.contoso.com' PrivateKeyExportable $True
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The private key is generated when the request is made. This key remains on the server that generates the request and is not provided to the third party. However, the PrivateKeyExportable flag indicates that you want to allow the private key to be exported and moved to another machine; this allows the single SAN certificate to be used on multiple hosts if mail.contoso.com, autodiscover.contoso.com, and legacy.contoso.com are actually separate machines. When you receive the SSL certificate, you can import it into Exchange with the Import-ExchangeCertificate cmdlet and then assign the certificate to the services that it should support with the Enable-ExchangeCertificate cmdlet. Alternatively, you can use EMC to complete the pending request that you generated with the wizard or the New-ExchangeCertificate cmdlet.
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11
INSIDE OUT
Minimizing the number of hostnames
In addition, it s a good idea to minimize the number of hostnames with which clients have to deal by using split DNS to provide different addresses for the same name for Internet and intranet access . This allows you to have the same name (such as m c ail . ontoso .com) no matter where a client accesses the service from .
Outlook Anywhere
Outlook Anywhere
Outlook Anywhere is the component of Exchange 2010 that allows Outlook clients to connect to Exchange from the Internet using HTTPS. Basically, Outlook wraps the RPCs that it usually uses to connect to Exchange in an outer layer of HTTPS that can pass through firewalls. The CAS server strips the HTTPS and redirects the RPCs to the correct mailbox server. This solution avoids the need for clients to use VPNs to communicate with Exchange and the need for administrators to open up additional ports in corporate firewalls. Outlook Anywhere is not enabled by default. You have to enable it on a CAS server in an Internet-facing Active Directory site to act as the initial entry point for client connections. You also need to enable Outlook Anywhere on at least one CAS server in every internal site. To enable Outlook Anywhere on a server, follow these steps:
1. Go to the Server node in EMC. 2. Select the CAS server. 3. Select the Enable Outlook Anywhere option in the action pane.
Figure 11-6 illustrates the Enable Outlook Anywhere Wizard. The options are very straightforward:
The external host name is the name that Outlook clients use to connect to the Outlook Anywhere service. Typically, the same name is used for all external points used for email access so that the same SSL certificate can be shared among Outlook Anywhere, ActiveSync, and OWA. The client authentication method determines how Outlook clients will authenticate themselves to Exchange when they initiate a connection. The default is basic authentication, meaning that the username and password are transmitted in plain text over an SSL connection. Most deployments use an advanced firewall such as Microsoft Threat Management Gateway that supports NTLM and can therefore enable this authentication method. The Allow Secure Channel (SSL) Offloading check box can only be selected if a separate server is used for SSL decryption and encryption. This server will be in front of the CAS server and will terminate the incoming connections and create new connections to send on for processing by the CAS. You ll normally use this option when you have a hardware load balancer or SSL accelerator that terminates or bridges SSL connections itself.
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