What determine whether I see 'keep both' or 'skip/stop/replace' as options when moving files??

Recently I've rolled over the file numbers on my camera again, so moving new photos around often causes filename conflicts:  'An item named "_XXX1234.jpg" already exists in this location.  Do you want to replace it with the one you're moving?"
What controls whether I see "Keep both files" as an option (where Finder just adds a 2 suffix to the filename of the newer item being added) vs "skip/stop/replace"? 
When I'm trying to copy distinct new items with duplicate filenames, I want to use 'keep both files'; when I'm grabbing a mass of files, moving to a common storage place, and want only the new files to copy over, so that finder does the hard work of figuring out which ones are new/missing from the new folder, I want the option of 'skip' instead.

The option-click 'copy file' does  not change the dialog box from just clicking and dragging without option--still only seeing the skip/stop/replace.
I do use iPhoto, but find the file structure does not follow my patterns of use, so do not let it organize the files--for those many, inevitable times when I want to access the images directly without having to export the images first.  I also have Adobe Bridge, which has a file renaming feature.  But I started seeing this option of 'keep both' recently--I think since my install of Mavericks when 10.9.3 came out, and determined it does something very helpful to me, but can't figure out how to make it show up consistently.  For some things it would be nicer than always just making a new iPhoto library when the file numbers start over again. 

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