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Securing Exchange Outlook Web App with ISA Server 2006 (part 1) - Exporting and Importing the OWA Certificate to the ISA Server

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OWA is one of the most commonly secured services that ISA servers protect. This stems from the critical need to provide remote email services while at the same time securing that access. The success of ISA deployments in this fashion gives tribute to the tight integration Microsoft built between its ISA product and Exchange Server product.

An ISA server used to secure an OWA implementation can be deployed in multiple scenarios, such as an edge firewall, an inline firewall, or a dedicated reverse-proxy server. In all these scenarios, ISA secures OWA traffic by “pretending” to be the CAS server itself, scanning the traffic that is destined for the CAS for exploits, and then repackaging that traffic and sending it on, such as that illustrated in Figure 1.

Figure 1. Explaining OWA publishing with ISA Server 2006.

ISA performs this type of OWA securing through an Exchange Web Client Access rule, which automatically sets up and configures a listener on the ISA server. A listener is an ISA component that listens to specifically defined IP traffic, and processes that traffic for the requesting client as if it were the actual server itself. For example, an OWA listener on an ISA server would respond to OWA requests made to it by scanning them for exploits and then repackaging them and forwarding them on to the OWA server itself. Using listeners, the client cannot tell the difference between the ISA server and the OWA server.

ISA Server is also one of the few products that has the capability to secure web traffic with SSL encryption from end to end. It does this by using the OWA server’s own certificate to reencrypt the traffic before sending it on its way. This also allows for the “black box” of SSL traffic to be examined for exploits and viruses at the application layer, and then be reencypted to reduce the chance of unauthorized viewing of OWA traffic. Without the capability to scan this SSL traffic, exploits bound for an OWA server could simply hide themselves in the encrypted traffic and pass right through traditional firewalls.

Exporting and Importing the OWA Certificate to the ISA Server

For ISA to be able to decrypt the SSL traffic bound for the Exchange CAS server, ISA needs to have a copy of the SSL certificate used on the CAS server. This certificate is used by ISA to decode the SSL packets, inspect them, and then reencrypt them and send them on to the CAS server. For this certificate to be installed on the ISA server, it must first be exported from the CAS Server from IIS Manager. By opening up the certificate and then right-clicking and choosing to Export the certificate, it can be exported to a .pfx file. Be sure to select to export the private key, as shown in Figure 2.

Figure 2. Exporting the SSL private key.


Caution

It is important to securely transmit this .pfx file to the ISA server and to maintain high security over its location. The certificate’s security could be compromised if it were to fall into the wrong hands.


After the .pfx file has been exported from the CAS server, it can then be imported to the ISA server via the following procedure:

1.
From the ISA server, open the MMC console (Start, Run, mmc.exe, OK).

2.
Click File, Add/Remove Snap-in.

3.
Click Add.

4.
From the list shown in Figure 3, choose the Certificates snap-in and then click Add.

Figure 3. Customizing an MMC Certificates snap-in console for import of the OWA certificate.


5.
Choose Computer Account from the list when asked what certificates the snap-in will manage, and click Next to continue.

6.
From the subsequent list in the Select Computer dialog box, choose Local Computer: (the computer this console is running on), and click Finish.

7.
Click Close and then click OK.

After the custom MMC console has been created, the certificate that was exported from the CAS server can be imported directly from the console via the following procedure:

1.
From the MMC Console root, navigate to Certificates (Local Computer), Personal.

2.
Right-click the Personal folder, and choose All Tasks, Import.

3.
When the wizard begins, click Next past the Welcome Screen to continue.

4.
Browse for and locate the .pfx file that was exported from the CAS server. The location can also be typed into the File Name field. Click Next.

5.
Enter the password that was created when the certificate was exported, as illustrated in Figure 4. Do not check to mark the key as exportable. Click Next to continue.

Figure 4. Installing the OWA certificate on the ISA server.

6.
Choose Automatically Select the Certificate Store Based on the Type of Certificate, and click Next to continue.

7.
Click Finish to complete the import.

After it is in the certificate store of the ISA server, the OWA SSL certificate can be used as part of publishing rules. Note that any Exchange Server 2010 SSL certificate that uses Subject Alternative Names (SAN) as part of the certificate requires at least ISA Server 2006 Service Pack 1 to use the SAN names in Web Publishing rules.

Note

If a rule that makes use of a specific SSL certificate is exported from an ISA server, either for backup purposes or to transfer it to another ISA server, the certificate must also be saved and imported to the destination server, or that particular rule will be broken.

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