Why not at logon, if you delete the profiles older than a certain amount of time? I use a cleanup script at logon, which 'cleans' profiles for a part: we keep 'Local Settings\Application Data' and the ntuser.* files.

We use roaming profiles and Outlook 2003 (ahumm) as a mail client and if we completely remove the profile, Outlook gives an error when a older user (profile dir earlier deleted) logges on. Somehow Outlook needs some files in the 'Local Settings\Application Data' directory.
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Kind regards,