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I found for Illustrator that having multiple copies of older version of Illustrator was confusing the ExtendScript Debugger. I ended up deleting all the old copies of Illustrator, uninstalling Illustrator and then reinstalling Illustrator, then debugging started working. I had also renamed the Illustrator apps to add the version number so I could tell them apart. Not sure what exactly caused my trouble, reinstalling seems to have fixed things.