Earlier this week, it was reported that on the Windows 10 October 2018 Update, users are having some trouble with ZIP files. As it turns out, when you try to extract a ZIP file and there are already files with the same name, there's no dialog box that appears asking if you want to overwrite them.
Today, Microsoft acknowledged the issue, detailing the problem and what you can do as a workaround. For one thing, the issue can happen when copying or moving data to a regular folder, or when copying to a regular folder.
Although the dialog box doesn't appear, the files are not overwritten. However, you'll want to be careful when actually moving files out of a ZIP file. Remember, ZIP files are opened as a directory, so you can move files out of them. If you try to move them to a folder where a file of the same name exists, it will not overwrite the file, but it will delete the original file.
The workaround is exactly what you'd guess, which is to use common sense. For now, only extract ZIP files to a new location, so it won't fail. Also, you shouldn't try cutting and pasting files at all, as those files might not be recoverable.
Microsoft pulled the Windows 10 October 2018 Update from servers on October 6, four days after it was released. While Insiders are testing some fixes for the original issues, it has still not been re-released.