Outlook email, contacts and calendars do not follow the user between workstations when you are using Roaming Profiles, which is a real pain. This is caused by the fact that Outlook stores its PST files, which contain all of these details, in the Local Settings profile folder, which is not transferred to the server. With Exchange, this isn't a problem, because everything is stored on the server, but in other circumstances this can be a problem.
Aside from groupware, the solution is quite simple: you can move the PST files to a new location on the server. This new location might be the user’s home folder (perhaps unwise given a user could accidentally delete all of his Outlook settings in a split second), or a folder in a separate ibay that is invisible to the user.
To move the PST folders:
1. Set up Outlook as normal
2. Close Outlook
3. Open the default PST storage folder, which is %userprofile%\Local Settings\Application Data\Microsoft\Outlook
4. Move any PST files to their new location on the server
5. Restart Outlook. Outlook will prompt you for the new location of the PST file(s)
If you have not previously moved the AutoArchive PST file (archive.pst), you will need to specify where Outlook should create it once automatic archiving is enabled.
1. Open the Options dialog and go to the Other tab
2. Click AutoArchive to open the configuration dialog
3. Turn archiving on
4. In the Move old items to field, specify the desired location of the archive PST folder
5. Restart Outlook.
When the user logs in to Outlook on another computer, her Outlook data will be available without further configuration. Once the PST file is stored on the server, it will also be backed up on a regular basis (assuming you do backups!), making it easier to retrieve messages that have been removed from the Deleted Items folder.
Note: If the server is unavailable or the share location changes (for example if drive mappings change), Outlook will break and prompt the user for the new location of her PST files.
This was tested in Outlook 2007 but should work in Outlook 2003 as well. Before that YMMV.