Autodiscover will configure the following services within outlook:
- Out Of Office
- Outlook Address Book
- Unified Messaging
- Availability Service (Free Busy)
- Exchange Control Panel
The issue was reproduced with the following settings:
School1 has a domain name of school1.edu. They host email at hoster1.com. School1 uses the "srv" method of locating the autodiscover record for autodiscover.hoster1.com.
What was broken
There are 200 different schools who are using the above mentioned configuration. We discovered a trend with customers having errors with OOO, OAB, and FreeBusy. This occurred for Outlook 2007 SP2 and newer clients who were previously on Exchange 2003, and migrated to 2010. All the profiles were set up manually.
Outlook 2003 was unaffected, since it uses Public Folders.
How we fixed it
The guidance was for the helpdesk to check the SRV record and correct it as necessary. In a majority of the cases, the SRV record was invalid or missing. The trick was
to ensure that both external and internal DNS was updated with the correct SRV record (in the event school1.edu also had an internal DNS)
Lastly, due to how outlook first checks for an A record at autodiscover.school1.com, some DNS servers returned the results of a wildcard entry. Removing the wildcard fixed the issue. For people who want to keep the wildcard DNS entry, they may want to try creating the autodiscover.school1.com record as a CNAME or an A instead of an SRV (though I haven't tested it)