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Windows Server 2012 R2 File Path character limit

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I know that the character limit is 256, however I ran into an issue that has me confused.

I have a Windows Server 2012 R2 Server with a Shared Folder on F:\ called FileShare.  FileShare has a subfolder Users.  I mapped a drive to my user folder \\Server\FileShare\Users\abcdefg to O:\ on a Windows 7 Workstation.  On the O: drive, I created a txt file with a file name that was 251 characters in length (that was the max before it wouldn't let me type anymore).  I received no errors.  Once you ad the ".txt", the 255 character limit is reached.  

Now comes the confusing part.  When I go on the file server, the actual file path is 277 characters because the file resides on F:\FileShare\Users\abcdefg.  When I right click on the file I only get Open, Print, Edit, Open with, and Send to as menu options.  I can not delete nor shift+delete the file from the file server itself.  

Why was I allowed to create a file name that long in the first place?  How can I remove a file like this from the server itself?


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