Moving multiple files with name auto resolve

You can hold down the option key to see the 'keep both' option with more than 3 files.

You could probably do it with a Unix utility. Some Linux utilities don’t work on Unix or aren’t available.

rsync would do it, but it is a bit complicated. There may be a tutorial on the web.

Take a look at this OSX Daily article on ditto. https://osxdaily.com/2014/06/11/use-ditto-copy-files-directories-mac-command-line/

If the destination folder is on a volume formatted for Macs you'll get a warning like this that duplicate names are encountered and if you want to keep both, replace or cancel.

If you keep both the duplicate will have copy at the end of the name:

You can then use You can then use Name Mangler to search for copy and replace that with whatever you'd like:

Unless your Mac is incorrectly formatted for a case-sensitive filesystem, only one filename can exist in a given filesystem location without the Finder assigning a generation set as a suffix (e.g. foo 2.txt). That said, I do not understand your comment about:

"I am trying to move a couple of hundred files from one folder to another and most of the names are duplicated even though most of the files are not."

Can you clarify that statement?

You can have two filenames that are different and contain the same data and no macOS move/copy solution will attempt to reconcile duplicate data in different filenames. The default behavior for a macOS Terminal-based move (mv) operation is to overwrite files during a move, though it does have a "-n" switch to prevent overwrites.

MacOS is based on flavors of BSD UNIX, and although there may be Linux commands with the same name, the Free Software Foundation (GNU) has seen fit to add additional or conflicting named switch arguments to these applications that produce different results even for the same switch argument. Unfortunately, the majority of Google searches that post solutions are from those using Linux, and not macOS with wrong or impossible results.

Hope with Apple is not a strategy and you need to inform the macOS product team of your need for a feature enhancement. These are fellow user supported public communities and the Apple product teams do not participate here and will not read your post.

Feedback - macOS - Apple

Do not assume that busy Apple support staff will do what they say. You and only you should send feedback to the product team in your own words so a). it is truly done, and b) not a misrepresentation by someone else of what you said they are attempting to reconstruct from memory or brief notes.

What you are experiencing is programmed into Finder and only the macOS product team could alter the behavior of that Finder dialog on larger quantities of files. I am unaware of any Finder workaround to get the low volume move dialog to apply to higher volumes of files.

Your approach multiplied by a couple hundred files might be considerable post processing effort.

The direct feedback link to the macOS Product team.