No, he simply has "File name extensions" hidden in Explorer (it is highly recommended to change that...). You can see the "Type" shows as "DRUME File".
As for the 404 error, it's an anomaly based on the files that were listed there. When the decryptor sees the STOP Djvu filemarker ("{36A698B9-D67C-4E07-BE82-0EC5B14B4DF5}") in a file, it takes the extension and asks the server "hey, is this Old or New Djvu?" (if it hasn't already asked for that extension). Apparently, those files had the filemarker, but no appended extension. There seems to be a security thing with the server engine that instantly rejects image extensions such as ".gif" for that parameter instead of letting my code handle it. I'll look into it, but it may be out of my control for the time being. Either way, it doesn't affect you much since those files were just in your Recycle Bin.
As the decryptor told you for your .drume files, it is Old Djvu, and you need to follow the instructions for uploading file pairs as Amigo-A said. You specifically need to upload an encrypted/original file pair for either a DOCX/XLSX/PPTX, or ZIP file, as those all start with the same first 5 bytes (which is why it is telling you what they are).
Edit: the 404 error has been fixed.