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Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004

Because of the release of the iPhone, there has been an increase in interest in configuring IMAP and POP3 services on SBS servers. In this author's opinion, providing access to e-mail via IMAP is better than POP3. The approach of IMAP more closely emulates how Exchange provides e-mail services in that messages are maintained on the server, and the IMAP client only pulls down what is needed.

There are still security issues with IMAP, however, in that the default protocol still transmits the username and password information across the internet in clear text, and even though fewer sniffers are trained on IMAP ports to try and discover account credentials, the risk is still there.

To help protect account credentials, as well as e-mail contents, IMAP can be set up over SSL, which encrypts the entire transaction process, not just username and password. The iPhone and other devices can be easily set up to use IMAP over SSL, but you have to first set up the Exchange server on SBS to provide the secure mail transport. This document covers this implementation with SBS 2003 and ISA 2004. A separate document has been created for the process to follow with SBS 2003 Standard.

Follow these steps to enable and configure IMAP using SSL.

  1. Enable the IMAP service on SBS 2003
    1. Open the Services control panel (Start -> Run -> services.msc or Start -> All Programs -> Administrative Tools -> Services)
    2. Scroll down to find Microsoft Exchange IMAP4 .
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    3. Double-click on the service to open the properties.
    4. In the General tab, change the Startup Type to Automatic.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    5. Click Start to start the IMAP service.
    6. Click OK to close the Properties window.
    7. Confirm that the IMAP service is started and set to Automatic in the services list.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
  2. Configure IMAP services in Exchange
    1. Open Exchange System Manager (Start -> All Programs -> Microsoft Exchange -> Exchange System Manager).
    2. Expand Servers, your server name, Protocols, and IMAP4.
    3. Select the Default IMAP4 Virtual Server, right click and select Properties.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    4. Select the Access tab, then click on the Certificate button under "Secure communication".
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    5. Go through the Web Server Certificate Wizard. Click Next to start.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    6. Select "Assign an existing certificate" and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    7. Select the public certificate name and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    8. Verify the proper certificate has been selected and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    9. Complete the wizard by clicking Finish.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    10. Select the "General" tab and click the "Advanced" button.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    11. Confirm the ports for IMAP are 143 and 993 (for SSL) and the IP address is "All Unassigned".
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    12. Click OK to close the Advanced dialog box, then click OK to close the properties of the IMAP4 Default Virtual Server.
  3. Enable SSL connections for the SMTP service
    1. Open Exchange System Manager.
    2. Expand Servers, your server name, Protocols, SMTP, and select the Default SMTP Virtual Server.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    3. Right-click on the Default SMTP Virtual Server and select Properties.
    4. Select the Delivery tab, then click Advanced.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    5. In the "Fully-qualified domain name" field, enter the full public DNS name of the server and click OK.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    6. Select the Access tab and click the Certificate button under "Secure communication".
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    7. Select "Assign an existing certificate" and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    8. Select the public certificate name, and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    9. Confirm the correct certificate selection and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    10. Click Finish to complete the wizard.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    11. In the Access tab, click Communication under "Secure Communication."
    12. In the Security dialog box, ensure that the "Require secure channel" checkbox is turned off.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    13. Click OK to close the Security dialog, then click OK to close the Default SMTP Virtual Server properties.
  4. Configure ISA 2004 to accept connections for IMAP SSL
    1. Open the ISA 2004 Management Console.
    2. Select Firewall Policy in the left pane, then select the Tasks tab in the right pane.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    3. Click the Create New Server Publishing Rule task to start the wizard.
    4. Name the new rule and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    5. Enter the internal IP address of the SBS server as the Server IP Address and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    6. In the Select Protocol page, select IMAPS Server from the drop-down list and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    7. In the IP Addresses page, select the External checkbox and click Next.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    8. Review the settings and click Finish to complete the wizard.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004
    9. Click Apply to accept the updates, then close the ISA 2004 Management Console.
      Configuring IMAP over SSL with SBS 2003 Premium and ISA 2004

At this point, you are able to make SSL connections to both the IMAP4 service as well as the SMTP service.

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