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Long file name errors could be happening because of the disk format. The first thing that I would confirm is that the file system can handle long file names.
Sometimes, when I copy my stuff to an external drive, some files are not copied. A message says that it cannot be copied because they have a long file name. I don't understand why this should be a problem and anyway, what can I do since I need to copy those files too? Often it's hard to specify their locality and if they are many, forget about it! Windows 7, 64, but in previous versions, I've had the same problem.
In this excerpt from Answercast #69, I look at possible reasons a drive would not be accepting files with long file names.
The problem is the format used on the external drive.
Realize that Windows (and DOS before it) began supporting only file names with eight characters - followed by an up to three-character extension after the dot. That's why so many of the operating system files are eight characters-dot-three because of simply legacy. That's the only way things could be.
Now, at one point, they added long file name support to the operating system. That required that the disk format actually be changed to be able to handle long file names - where file names could be up to something like 255 characters long with an arbitrary amount of periods, the extension could be any length, and so forth.
The problem is then that if you have one of these hard drives or one of these external drives that is using a disk format that does not support long file names - well, you can't copy files that have long file names to that drive.
So, what I would recommend you do is:
Double-check the format of the external drive that this happens to;
And if appropriate (in other words, if all the systems that it might be connected to can support it), convert that drive to NTFS.
Most versions of FAT will handle long file names. Older versions of FAT do not - and quite honestly, I'm kind of surprised that you're running into this.
NTFS, by definition, will handle long file names. It's a simple "convert command" to actually convert the external drive from one file system format to another.
I have an article on how to convert that. It's a command you run in a Windows Command shell. The net result is that you will have a disk that uses NTFS instead of the FAT file system and then it can use or support long file names.
The only other thing I can think of that might cause you to run into this problem is if indeed your file names are multiple hundreds of characters long - or if the combination of the file folders and the file name exceeds something like 256 or 512 characters long.
In other words, the entire path to a file has a limit on it as well.
So, I recommend you certainly look at those scenarios when it's reporting the
error. But if it's happening regularly, if it's happening on one specific
device, the first thing that I would confirm is that the file system on the
device you're copying to can in fact handle long file names.
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