Assuming that all of the picture files are located in the Pictures folder, this following AppleScript code should work. Paste this following code into a new Script Editor.app document. You can run the code directly from that document or you can save the code as an application and run the application like you would with any other app. activate set picturesFolder to choose folder with prompt ¬ "Choose The Folder Containing Your Pictures" with invisibles activate set categoriesFolder to choose folder with prompt ¬ "Choose The Categories Folder" with invisibles tell application "Finder" activate set pictureFiles to files of picturesFolder as alias list repeat with i from 1 to count of pictureFiles set foldersRef to (a reference to folders of categoriesFolder) set foldersRefItems to name of (contents of foldersRef) set thisItem to item i of pictureFiles set fileName to (text items 1 thru -5) of (name of thisItem as text) as string if fileName is not in foldersRefItems then ---- This Will Create Aliases To The Original Files ---- ---- Much Quicker And Space Efficient Than Duplicating The Files ---- make new alias file at (make new folder at categoriesFolder ¬ with properties {name:fileName}) ¬ to thisItem with properties {name:fileName} ---- Un-Comment The Next 2 Lines If You Prefer To Duplicate The Files ---- -- duplicate thisItem to (make new folder at categoriesFolder ¬ -- with properties {name:fileName}) else try ---- Un-Comment The Next Line If You Prefer To Duplicate The Files ---- -- Duplicate Thisitem To Folder Filename Of Categoriesfolder -- make new alias file at categoriesFolder ¬ to thisItem with properties {name:fileName} end try end if end repeat end tell