Folder refuses to be moved to Recycle Bin under Windows 7

I have a folder with files for the project I work with. I move it from my desktop to laptop and back, almost every day, depending on which machine I use it on at the time. The process of the move is very simple: I ZIP the folder, put it on USB stick, then go to the destination machine, move the old folder into the Recycle bin and paste the new one from the ZIP archive.

But lately when I do the move to the Recycle bin I get the message, "Do you want to permanently delete this folder?" and then "The folder contains items whose names are to long for the Recycle Bin."

I'm not sure what did I do, because that message wasn't shown before?

PS. I prefer to keep old folder in the Recycle bin, just in case I need to undo something later.

Answer

If you have too many nested folders leading to an extra-long path, you'll get such errors.

You can shorten the names of your folders at each level to prevent this sort of issue.

You can also try renaming the folder to "Foldername_Old" or something instead of deleting it, then copy the new version over.

If you have problems deleting the folder, use the \\.\ alternate syntax as detailed here and here, or the RoboCopy trick detailed here and here.