Long file names

Hello all, I realize the 255 character limit still exists in 2008 R2, but what I dont' understand is how windows will sometimes allow files with names longer than supported?

Consider this path:

D:\DATA\Enterprise Risk\Clients\Business Entity\c\City of Bluebun(RISK) - 123456\City of Bluebun 2010-123456\Working Papers\Deliverable 3 - BIA\BIA Interviews\Solutions Development and Sustainment\Solutions Development and Sustainment - Time Criticality Summary Table.docx

This path exists on a server in my organization, there are 272 characters in that path. When I try to restore from shadow copy, I can't. I have to restore to a different directory, like D:\Temp, then remove enough characters from the filename that allows me to copy it to that directory. In this case, Solutions Development and Sustainment - Time Criticality is as long as I can make the file name. So, how can a file that is longer than the supported length even get put there in the first place?

I need to explain to my users that the limitation is 255 characters, but also explain how they got a file there with 272 characters in the path.

"D:\Data\Enterprise Risk" is shared out as "\\12345fs1\enterprise_risk$" to the users, mapped as the y: drive. I have tried mapping this drive as the users would see it to restore from Shadow, thinking it might have something to do with the drive letter shortening of the path, but I can't copy the file in to this directory, without removing 27 characters.

So, clearly windows allowed this long file to be put there, but now will not allow it to do this again. There are no applications involved other than Word or Excel, so this is 100% Microsoft going against it's own rules. At least that is how it would seem.

This happens on multiple servers in my organization, Server 2003, Server 2008, Server 2008 R2.

Also, I understand there is redundant text in this path, but my users would understand the issue more if they were presented with this problem at the time of creating the files.