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Roaming profiles and 'cannot copy file due to filename or extension is too long'?

We have a Windows 2008 R2 file server, and our clients are Windows 7 machines mostly. They are all in the same domain. I've noticed that an user has trouble with his roaming profile due to the filename or extension of files synced being too long. And this isn't exactly the first time either.

User Profile General - Event id 1509:

"Windows cannot copy file \\Synsrv1$NOCSC$\Synocus Users\KenI\Profile.V2\Documents\Visual Studio 2010\Projects\EmployeesVisualWebPart1\EmployeesVisualWebPart1\pkg\Debug\EmployeesVisualWebPart1\CONTROLTEMPLATES\EmployeesVisualWebPart1\EmployeesVisualWebPart\EmployeesVisualWebPartUserControl.ascx to location C:\Users\KenI\Documents\Visual Studio 2010\Projects\EmployeesVisualWebPart1\EmployeesVisualWebPart1\pkg\Debug\EmployeesVisualWebPart1\CONTROLTEMPLATES\EmployeesVisualWebPart1\EmployeesVisualWebPart\EmployeesVisualWebPartUserControl.ascx. This error may be caused by network problems or insufficient security rights.

 DETAIL - The filename or extension is too long."

I've checked for the file on our file server, and it's simply not there. Apparently it has never been synced to the file server, probably due to the filename or extension being too long.

The solution, as presented in a similar thread (https://www.experts-exchange.com/questions/22600828/Event-ID-1509-Cannot-Access-Roaming-Profile.html), is to create a new profile and copy all important content. Alright, that's doable...

However, I'm not looking for the quick fix, but rather to the cause of this issue. Is there any way to get rid of the 'filename or extension is too long' bug in the first place? As we cannot control the folders each application creates, I'm hoping to find a way to be able to copy long filenames and extensions.
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Synocus

ASKER

Confirmed, the troublesome long filename files were never synced to the file server, and from that point on the profile sychronization started failing, and as the files were never removed they effectively made the user to keep running a profile that's stored locally only.

How can we prevent this issue from repeating?
ASKER CERTIFIED SOLUTION
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Hypercat (Deb)
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