I have a very deep directory hierarchy for our java code and we have some long classnames and classes that have inner classes with long names. Anyway, after running a build, I found that I could not delete the classes. There was 1 file that Windows couldn't delete. When I tried to delete it Windows said file not found. Yet I could not delete the directory because there was a file in the directory. I rebooted ran checkdsk, nothing. I tried deleting from the command line, using 4nt, using rm -rf nothing worked. Finally, I realized that the path of the file was > 256 characters. After googling I found that rd /s on the directory where the file lives works.
This was really bizarre. Windows allowed me to create a file whose path was > 256 characters and then couldn't deal with it. Why is a Windows 2000 NTFS file system limited to a path of 256 characters?