Litigation Support Tip of the Night has addressed in the past the well known 255 character limit on file paths in Windows. See the Tip of the Night for October 10, 2015, which discussed how to handle file paths longer than 255 characters [the limit actually concerns what Windows Explorer can deal with, not what directories can exist in a Windows operating system] with the subst command and the Tip of the Night for April 18, 2016 which shows how a utility from Replsoft which will automatically detect and truncate paths exceeding the limit.
Windows 10 will save us all the headache of dealing with long file paths. Microsoft's new operating system includes an option in the Group Policy Editor to enable the default NTFS file system to handle long file paths. To access the group policy editor press the Windows key + R, and enter gpedit.msc.
Under, Local Computer Policy > Computer Configuration > Administrative Templates > System > Filesystem > NTFS, click on 'Enable NTFS long paths'.