Why is "Keep Both" not available when copying search results in Finder? (macOS Sequoia 15.5)

Hi everyone,

I’m using a MacBook Pro with macOS Sequoia 15.5 and have run into an issue with Finder that’s disrupting my workflow.

Issue:

When I search for files within a large folder structure in Finder and then try to copy the search results into a new folder, I often have several files with the same name (e.g., “IMG_0001.jpg” from different subfolders). When I paste these files into the new folder, Finder only gives me the options to “Skip,” “Replace,” or “Stop” if there’s a filename conflict.

The usual “Keep Both” option, which automatically renames one of the files, does not appear in this scenario.

This is different from what happens when copying files from a regular folder view, where “Keep Both” is offered, and Finder creates uniquely named copies (like “IMG_0001 copy.jpg”).

Question:

Is there a way to enable the “Keep Both” option when copying files from a search results list in Finder?

Or is this a known limitation in macOS?

Are there any workarounds or third-party tools that handle this situation more elegantly?

Any insights or tips would be much appreciated.

Thank you!