The Security Implications of Windows Volume Shadow Copy
It can be impossible to securely delete a file:
What are the security implications of Volume Shadow Copy?
Suppose you decide to protect one of your documents from prying eyes. First, you create an encrypted copy using an encryption application. Then, you “wipe” (or “secure-delete”) the original document, which consists of overwriting it several times and deleting it. (This is necessary, because if you just deleted the document without overwriting it, all the data that was in the file would physically remain on the disk until it got overwritten by other data. See question above for an explanation of how file deletion works.)
Ordinarily, this would render the original, unencrypted document irretrievable. However, if the original file was stored on a volume protected by the Volume Shadow Copy service and it was there when a restore point was created, the original file will be retrievable using Previous versions. All you need to do is right-click the containing folder, click Restore previous versions, open a snapshot, and, lo and behold, you’ll see the original file that you tried so hard to delete!
The reason wiping the file doesn’t help, of course, is that before the file’s blocks get overwritten, VSC will save them to the shadow copy. It doesn’t matter how many times you overwrite the file, the shadow copy will still be there, safely stored on a hidden volume.
Is there a way to securely delete a file on a volume protected by VSC?
No. Shadow copies are read-only, so there is no way to delete a file from all the shadow copies.