Perhaps you could encrypt the filenames with a user-supplied password hash. Upload and store just the encrypted filenames, and when the user is viewing the data

Perhaps you could encrypt the filenames with a user-supplied password hash. Upload and store just the encrypted filenames, and when the user is viewing the data on the web can decrypt the filenames by asking them for the filename password. You could run analytics on the encrypted data still, and not expose filenames to even wakatime.