I did some workaround on this behavior by adding an event listener on the dialog box via JS. This way the callback will be triggered. window.addEventListener("beforeunload", function (e) { sketchup.focus_dialog() }, false); @dlg.add_action_callback('focus_dialog') do |ac| @dlg.bring_to_front end

Thank you for your help! Turns out the camera that the photos were taken off of had some weird GPS offset, which is why my photos were imported yet placed kilometers away. I solved my problem by using a 'reference point'. I have the user import one photo and place that photo where they believe it was taken. I use that photo's lat and long to modify the rest of the photos that were imported. Success