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Using Windows Easy Transfer is amazing tool for when you want to move all your profile settings and personal files from your old system to your new one.
But like everything it’s not perfect, for instance you can’t go from 64 bit – 32 bit (Who would want to…)
You can’t go from WIndows 7 to Windows 8 (Yes it’ll copy your files but not your settings, should be expected, and only via USB HDD)

and one pet pieve that it doesn’t copy over Outlook sugnatures given its located under a user profile directory (C:\Users on Vista and up versions)

Now copy the files from %APPDATA%\Microsoft\Signatures (%APPDATA% is C:\Users\useraccount\appdata\roaming)
Not to be confused with %localappdata% which is C:\users\useraccount\appdata\local

Since these files are hidden system files I suggest to use xcopy with the /i /e /h options.
You can also adjust Windows explorer folder view settings to show hidden and system files.

Once these Files have been copied to the destination machine with the same user at the same directory,
simply reopen outlook and check your signatures! Boom, they are back baby!

Jan 2018 Update Notes

First off, WET is no longer a thing. I will admit I am very sad to see it go, as a systems administrator it was a thing of beauty and made my life a breeze. Sadly now Microsoft has out sourced this to a partner company “Laplink’s PCmover Express“, and even worse it’s a paid product. I personally think its rubbish, you’d be better off updating/upgrading your software manually and simply moving any associated files with that application manually.

Secondly, You’ll notice the use of Environment Variables. Learn em, use em they are a vital tool to management specially with non-default directories or system drives.