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Configuring IMAP over SSL with SBS 2003 Standard

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 Standard and no ISA. You will need to configure your firewall to forward the appropriate ports to the SBS server, which is beyond the scope of this document

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 (see Figure 1).


Figure 1

  1. Double-click on the service to open the properties.
  2. In the General tab, change the Startup Type to Automatic (see Figure 2).
    Figure 2
  3. Click Start to start the IMAP service.
  4. Click OK to close the Properties window.
  5. Confirm that the IMAP service is started and set to Automatic in the services list (see Figure 3).
    Figure 3
  1. Configure IMAP services in Exchange
  2. Open Exchange System Manager (Start -> All Programs -> Microsoft Exchange -> Exchange System Manager).
  3. Expand Servers, your server name, Protocols, and IMAP4.
  4. Select the Default IMAP4 Virtual Server (see Figure 4), right click and select Properties.
    Figure 4
  5. Select the Access tab, then click on the Certificate button under “Secure communication” (see Figure 5).
    Figure 5
  6. Go through the Web Server Certificate Wizard. Click Next to start (see Figure 6).
    Figure 6
  7. Select “Assign an existing certificate” and click Next (see Figure 7)
    Figure 7
  8. Select the public certificate name and click Next (see Figure 8).
    Figure 8
  9. Verify the proper certificate has been selected and click Next (see Figure 9).
    Figure 9
  10. Complete the wizard by clicking Finish (see Figure 10).
    Figure 10
  11. Select the “General” tab and click the “Advanced” button (see Figure 11).
    Figure 11
  12. Confirm the ports for IMAP are 143 and 993 (for SSL) and the IP address is “All Unassigned” (see Figure 12).
    Figure 12
  13. Click OK to close the Advanced dialog box, then click OK to close the properties of the IMAP4 Default Virtual Server.
  14. Enable SSL connections for the SMTP service
  15. Open Exchange System Manager.
  16. Expand Servers, your server name, Protocols, SMTP, and select the Default SMTP Virtual Server (see Figure 13).
    Figure 13
  17. Right-click on the Default SMTP Virtual Server and select Properties.
  18. Select the Delivery tab, then click Advanced (see Figure 14).
    Figure 14
  19. In the “Fully-qualified domain name” field, enter the full public DNS name of the server (see Figure 15) and click OK.
    Figure 15
  20. Select the Access tab and click the Certificate button under “Secure communication” (see Figure 16).
    Figure 16
  21. Select “Assign an existing certificate” and click Next (see Figure 17).
    Figure 17
  22. Select the public certificate name, and click Next (see Figure 18).
    Figure 18
  23. Confirm the correct certificate selection and click Next (see Figure 19).
    Figure 19
  24. Click Finish to complete the wizard (see Figure 20).
    Figure 20
  25. In the Access tab, click Communication under “Secure Communication.”
  26. In the Security dialog box, ensure that the “Require secure channel” checkbox is turned off (see Figure 21).
    Figure 21
  27. Click OK to close the Security dialog, then click OK to close the Default SMTP Virtual Server properties.

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

Source from : http://www.smallbizserver.net/Default.aspx?tabid=266&articleType=ArticleView&articleId=231

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