Warning: Apple’s File Sharing panel in macOS 10.15 does not prompt you when you attempt to add a file with the same name as an existing file. With macOS 10.15, Apple restructured iTunes and split up its functionality into several different apps: Apple’s File Sharing panel can now be accessed directly through Finder. All Categories / Adding Files, General Troubleshooting, Getting Started, Sharing macOS 10.15 or later