Why not just use Preview?

Preview is genuinely capable, and for two small files it is fine. It becomes frustrating for three reasons that only show up once the job is real.

The workaround most Mac users land on — dragging thumbnails between two open windows — also fails silently when a source file has an outline, because the outline is attached to the document rather than to the pages you dragged.

  • You must have both sidebars showing, in thumbnail view, and drop pages precisely between two thumbnails. Drop onto a thumbnail instead of between two and you insert into the wrong place.
  • Bookmarks are lost. A merged file from Preview generally has no outline, which makes a long combined document hard to navigate.
  • It saves over the first document unless you explicitly export, so a mis-merge damages a source file.

Does it work with iCloud Drive files?

Yes, with one thing to watch. A file stored in iCloud Drive that has been evicted from local storage shows in Finder with a cloud icon and no local copy. Dragging it into a browser page can hand over a placeholder rather than the document.

Click the download arrow beside the file in Finder first and wait for the icon to clear. The whole file is then on the Mac and behaves normally.

The same applies to Desktop and Documents folders when "Optimise Mac Storage" is switched on.