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One single-name SSL certificate with a second HTTP redirection website
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Requires one single-name SSL certificate
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One single-name SSL certificate for Autodiscover and OWA using Autodiscover name (autodiscover virtuecorpcom) One single-name SSL certificate with DNS SRV lookup
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Simple configuration Requires: One website One public IP One single-name SSL certificate Simple configuration Requires: One website One public IP One single-name SSL certificate
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Not all DNS hosting providers support DNS SRV records An additional dialog box is displayed to the Outlook users asking if they trust the redirected URL Requires Outlook 2007 client-side hotfix 939184 Requires all users have Outlook 2007 External Autodiscover won t work Users will see a certificate prompt when using OWA ActiveSync won t work correctly
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TABLE 8-6 Various Autodiscover Con gurations
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Administering Client Access Servers
As mentioned earlier, when you install Exchange, it creates a self-signed SSL certificate with a CN that matches the NetBIOS name of the server This won t have the desired effect when connecting externally, so we turn to commercial SSL certificates In previous versions of Exchange, you could install a certificate that matched the address your users would use for Outlook Web Access (such as mailvirtuecorpcom), and life was good In Exchange 2007, it s a little more complicated First, we have the URL for OWA, then we have the URL for Autodiscover and its related services Because a website in IIS can only have a single certificate, we have to choose how we want to make this work As mentioned in Table 8-6, various certificate solutions include the following: You can use what s called a Unified Communications Certificate, also known as a Subject Alternative Name certificate (or SAN certificate, for short) This is the preferred method because it keeps everything within one website in IIS and uses a single certificate This makes it easier to administer One problem with SAN certificates is that not all Certificate Authorities (CAs) can provide them See http://supportmicrosoftcom/kb/929395 for information on which CAs handle Subject Alternative Name certificates The other problem is that SAN certificates are considerably more expensive than traditional certificates Often up to ten times as much For smaller companies, it might not be feasible to purchase a SAN certificate You can split the Autodiscover virtual directory out from the default website and give it a website of its own This would allow you to use one certificate for OWA and one for Autodiscover, each with its own Common Name (CN) This requires an additional IP address to be configured in IIS, as well as the additional setup for multiple websites Use the same name for both Autodiscover and Outlook Web Access With this method, users would go to https://autodiscoverdomaincom/owa for OWA and would use https://autodiscoverdomaincom for Autodiscover Only a single SSL certificate is required Users would need to adjust to going to autodiscoverdomain com/owa for OWA, and that may cause confusion Redirect Autodiscover using an IIS redirect This requires additional setup, and the users still get a prompt when using Outlook asking whether they trust the redirected website Use the same URL for OWA and Autodiscover This would mean your users would use https://autodiscovervirtuecorpcom/owa for Outlook Web Access and https://autodiscovervirtuecorpcom for Autodiscover and Outlook Anywhere This method works fine, but users might not be able to grasp that OWA URL if they are already using a different one, such as https://mailvirtuecorpcom/ Use the original self-signed certificate Internally, Autodiscover will work fine Externally, users will be prompted with a certificate warning Additionally, mobile users may not be able to use ActiveSync on their mobile devices because the certificate is not trusted As you can see, there are many options and each brings its own pros and cons Once you ve decided which path to pursue, you can set out to get it configured In the remainder of this section, I ll cover the various configurations
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