I had an issue recently where Outlook 2010 settings and signatures were not being migrated to the new machine when using USMT in conjunction with SCCM OSD. There is a Microsoft hotfix for USMT 4.0 to specifically address this, essentially it is an update of the executables, DLLs and XML files to support the Office 2010 application. See http://support.microsoft.com/kb/2023591
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Just remember – if you apply this hotfix, you need to download download both versions of the hotfix (amd64 and x86) and copy the correct versions to the correct subfolders!
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