Character length of 255

While moving from W95 -> W2k with the following source:
* (c:\my documents\…)
to the target:
*(c:\documents and settings\username\my documents\…)
there have been times when the data would not copy over without shortening the file name.
I think the issue is tied to the user’s file name\folder paths being so long and deeply nested that the change in the “parent directory” (c:\my documents\ vs c:\documents and settings…) kicks the total character length beyond the 255 limit.

Is there a way around this issue other than having the user shorten their file or folder names?