As much as a I dislike Microsoft Outlook, we have a number of customers using it whom require support services and for the most part, it tends to meet their needs.
Like any Microsoft product, Outlook does have it’s own set of quirks and annoyances. In particular, the process of moving account mail and settings is much more complicated than competitors like Thunderbird who have a simple directory containing both config and files.
Whilst Outlook will use PST files for local email storage (don’t even get me started about PST files…) it doesn’t store the configration for accounts/settings as a file that you can copy across, so after moving to a new computer/account, the files can’t be re-imported.
This can be avoided if you use the windows migration tools, but these aren’t always appropriate for every situation, nor are they any use when you’re recovering selective bits of data from a backup.
The good news is that there is an (I think undocumented) way to copy the Outlook profile settings over to another computer/user.
To do so, run regedit and browse to the following location in the registry:
HKEY_CURRENT_USER\Software\Microsoft\Windows NT\CurrentVersion \Windows Messaging Subsystem\Profiles
Whilst it’s all just blob data, these registry values contain your account settings and details for Outlook. By exporting the profile(s) from this location you can then re-import onto the new account/computer to retain all your settings.
When Outlook starts, it will remember all the settings (excluding passwords) and if it can’t locate the PST files in their previous location, it will prompt for the new one.