I've been using Windows 7, Parallels 11 and El Capitan, so I can describe how this works for me. I've read that Windows Libraries are hidden by default on Windows 10, but can be enabled in Folder Options.
I have found that if you access Mac files from Windows through the Windows libraries - Documents, Music, Pictures, Videos - deleted files are moved to the Windows Recycle Bin. You will see Recycle Bins listed for Documents, Music, Pictures and Videos in the Recycle Bin properties. I suspect Parallels adds all those locations in there, or Windows adds them when it sees that some folders were added to the libraries that are not in the usual locations. So, those areas are under Recycle Bin protection. (In a standard Windows install on a PC, the Recycle Bin simply protects your C:\ (and D:\ etc.) drives - it doesn't need to do anything special to protect your libraries, since they are on drives that are already under Recycle Bin protection.)
But if you delete those same Mac files through the mapped drives (Y:\ or Z:\), or through the Network locations (\\Mac\Home and \\Mac\All Files) - they are deleted immediately. Windows does not recognize those areas as having Recycle Bins. That may explain the problem you are seeing.
That means - for the Recycle Bin to protect Mac files, you need to use shared profile and libraries, and not just the basic sharing.
Desktop is a special case, depending on whether or not you merge Mac and Windows desktops. I prefer to not merge my desktops, and haven't found a way to include the Mac desktop in a Windows library, so the only way to access an "unmerged" Mac desktop from Windows is through the mapped drives or network locations. And this means deleting a file from the Mac desktop or subfolders on it through Windows will result in an immediate delete. Unless you find a way to add the Mac desktop to a Windows library, by pulling the same magic that Parallels does to add Mac network locations to the standard Windows libraries, files there have to be deleted with more care. One could move such files to some folder in Documents before deleting them, for instance Documents\Deleted Desktop Items, or move them first to the Windows desktop, or just not leave files on the Mac desktop. (Files on the actual Windows desktop, if you use it, will still go, as usual, to the Recycle Bin, because they are on the protected C:\ drive.)
A merged desktop will probably work differently, but I disable that particular shared profile feature so I don't know.
I hope that wasn't too confusing!
As far as I can tell, Parallels doesn't not document any of this, nor discuss these topics in these forums. And I wouldn't be surprised if this works differently with different versions of Parallels, and different versions of Windows. As undocumented features, the things I've observed are probably subject to change at virtually any time.
But in the meantime this information might actually help somebody? I hope so.
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