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I have all my photos in Photos.app. I also maintain them in Dropbox.

My workflow is:

  1. Import from camera/iPhone into Photos
  2. Organize photos into albums - some into new albums, some into existing albums.
  3. Export unmodified originals from Photos to a folder structure that matches the album layout in Photos using File > Export > Export Unmodified Original

New albums are easy. Exporting the entire album is no problem since they are all new files. If I add images to an existing Photos album, I'd like to be able to simply export all of the photos in that album to the Dropbox folder. But if I do that, Photos makes a second copy of the image named "image000(1).jpg". I don't get prompted to overwrite or not overwrite existing files.

Is there a way to have Photos.app prompt me to overwrite existing files instead of creating duplicates? Perhaps a hidden plist setting somewhere I can modify...

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In my version of Dropbox for OS X, v3.4.3 (not the latest), it has a feature to automatically upload photos whenever you connect your devices.

It is in Dropbox's preferences, under IMPORT tab, first option Enable camera uploads for [photos and videos].

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