I was having this same issue. I was trying to import around 1,300 pictures from an old iPhone 4s to my MacBook Pro. It imported 300 pics the first time fine, but then got stuck, doing the below resolved it: Close the Photos app Open System Settings Navigate to Privacy & Security > Full Disk Access Click the + to add a new item Go to your Applications folder and select the Photos app Click open Make sure it is toggled on and reopen the Photos app After doing these steps, it imported all the pictures correclty except 100 that were left. To fix that, I closed the Photos app again, disconnected the iPhone, reopened the Photos app, and reconnected the iPhone. Then clicked 'import all new items' and it completed as expected. Hope this helps someone!