This is a service to help automatically configure Outlook 2007 profiles based soley on a user’s email address. This service also helps retreive the locations of new Exchange 2007 services such as free/busy, out of office, and web-based offline address book distribution.

For Internet Outlook 2007 users, the basics of this service are that they enter their email domain (name@emaildomain.tld) and Outlook automatically tries to connect to:

https://emaildomain.tld/autodiscover/autodiscover.xml
https://autodiscover.emaildomain.tld/autodiscover/autodiscover.xml
When retrieving settings from one of these URLs, HTTPS (SSL) is required — which means there must be a valid security certificate installed for that web site that matches the site name.

This, of course, poses an interesting problem for Exchange-based messaging hosters who do not want to have to buy a unique SSL certificate and set up a new web site for each new hosted domain. (If they are hosting mail for mycrazywidgets.org, they don’t want to have to buy a valid certificate for autodiscover.mycrazywidgets.org). This also may be an issue for corporate environments that host multiple email domains but do not wish to purchase a certificate for each one.

Luckily, we have a solution for this — that you can try out once Office 2007 Beta 2 Technical Refresh is released. (Check here, I think, for when it is released).

There are a set of “one-time” configuration steps for hosters to get going, and then a set of steps for each new email domain that you host:

One-time configuration steps for multi-domain hosting & AutoDiscover:

Create a new virtual web site (on a new IP) that is Internet-facing. Call it something like “autodiscoverredirect.[hosterdomain.tld]” where [hosterdomain.tld] is your ‘main’ domain name. {The actual name of this virtual web site isn’t really important}. No certificate is required for this web site.
Create an /autodiscover/ virtual directory on that web site.
Create an empty file in this directory called “autodiscover.xml”
Through IIS manager, configure that file to be a redirect to https://autodiscover.[hosterdomain.tld]/autodiscover/autodiscover.xml. (This can be set on the properties page of the file through IIS manager).
Per-domain configuration steps:

For each new hosted email domain

The DNS configuration of that email domain must be changed to add a CNAME record for “autodiscover.[emaildomain.tld]” pointed to “autodiscoverredirect.[hosterdomain.tld]”.
Given that you already have to make DNS changes to host a new email domain (i.e., configure the MX record), this should just be one small additional step in that existing process.

Client experience

Now, what happens when a user types in emailaddress@[emaildomain.tld] into Outlook 2007? This isn’t the complete list, but Outlook will:

Attempt to connect to https://emaildomain.tld/autodiscover/autodiscover.xml & fail.
Attempt to connect to https://autodiscover.emaildomain.tld/autodiscover/autodiscover.xml & fail.
Attempt to connect to http://autodiscover.emaildomain.tld/autodiscover/autodiscover.xml & succeed — but receive an HTTP-level redirect to https://autodiscover.[hosterdomain.tld]/autodiscover/.
Warn the user about this redirect and ask them if they trust getting their settings from [hosterdomain.tld]. (The warning can be turned off by the user after the first time). It says: “Allow this website to configure user@domain.tld server settings?” followed by the URL of autodiscover at the hoster domain. If the user does not recognize the hoster domain, then they should cancel.
If the user accepts, Outlook will then connect to https://autodiscover.[hosterdomain.tld]/autodiscover/ and retreive profile settings.

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