Hi,
Well, to set your expectations accordingly, you'll probably want to open a Support Incident on this issue. There are just so many variables that will need to be covered and checked. Enough that working the issue through a forum would be probably impossible.
But, I will throw what I can at you and hopefully it will help point the way to the resolution.
1. When you logged on and the Index started to rebuild, did you let it complete?
2. What is the location you're Indexing to? --Click File | Options | Search | Indexing Options | Advanced
- The default will be <Root drive>:\ProgramData\Microsoft
- I have no idea what this would be in a TS environment.
3. Was Outlook started on the Terminal Server while it was still in Install mode?
- I have seen that create a situation where user A logs on and uses Outlook. User A logs off and then user B logs on. The index Outlook sees is for user A. Since this is user B, the index needs to be built.
- Did you switch back to Execute mode before launching Outlook the first time? --You don't want to run Outlook (or any other Office applications, for that matter) in Install mode.
4. Please read through the following post. It's the same question you have except for Outlook 2007.
http://social.technet.microsoft.com/Forums/en-US/winserverTS/thread/92edb935-3e55-4db7-bd09-3b9e0aeb15f7
That's all I have. If this doesn't help, I would suggest calling in and opening Microsoft Support incident.
Please visit the following link for details on the various support options available to you:
http://support.microsoft.com/default.aspx?id=fh;en-us;offerprophone
Thanks!
Jahawk MSFT