I am having some issues with autodiscover which are very likely due to a misconfiguration. I am unable to use the out of office assistant in Outlook 2007. When I test the autoconfiguration of outlook 2007 (by right-clicking the outlook icon by the clock on win7 while holding ctrl and then choosing test email autoconfig), it fails if I use email@example.com, but works if I use firstname.lastname@example.org.
I have an internal A record in DNS pointing autodiscover.domain.com to the email server's LAN IP. I do not have an external DNS entry for autodiscover. I do not manage external DNS and have put in a request to add a DNS record for autodiscover.domain.com pointing to the 2010 exchange server's public IP. Not sure if that will matter here, but wanted to mention.
In IIS, default web site > autodiscover SSL settings are require SSL but ignore client is selected.
the autoconfig test shows the old 2003 server URL at mail.domain.com for Availability Service, OOF, and unified messaging, but OAB shows the correct URL of webmail.domain.com. Same thing under both Protocol: Exchange RPC and Protocol:Exchange HTTP.
Another thing is that in 2010 EMC, all default websites are set to webmail.domain.com and webmail.domain.com/owa works fine, as well as active sync. Further, the out of office assistant works in OWA. However, in IIS, default website are showing mail.domain.com under redirect, but they are all grayed out.
Any ideas how to clean this up and get out of office working properly, including having IIS show webmail instead of mail, are greatly appreciated.