de0u If you do this again, it would be useful to record roughly how many files
It was an encrypted backup so there were thousands of somewhat small files, around 7000 I think and ranging from a few kilobytes to a few megabytes, in 256 separate folders. It's probably a standard way to encrypt large archives, but I don't know the name of the format.
de0u Also, when the deletion "failed", what were the symptoms?
Some of the folders containing the files were deleted and some weren't. From what I could tell, they were being deleted in a seemingly random order. I didn't check to see if there were files being deleted in random folders. I also didn't check if there were files that were partially deleted when it failed, but I doubt it.
I "resumed" the deletion by pressing delete on the top-most folder.
de0u Was an error message displayed?
No, there was no error. The notification that usually says progress was saying "0/1" and "Deleting files". There was a progress bar, but it was empty the entire time and had no progress or time counter.
I hope this can help.