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Lost Files

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My husband upgraded to windows 10 more than a month ago.  Lost files and asked me to help.  It's over 28 days so the windows.old file is gone (or at least I can't find it).  I read that sometimes files end up there but it gets deleted after 28 days.  I've tried everything else suggested on the windows troubleshooting - files lost section.  Does this mean his files were probably in there but now gone forever? Or is there something else I could try to find them again?  No, he did not have a back up. 

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