that sounds like the screw is the wrong one, or the internal threads are stripped, or the screw was longer and part broke off inside. can you get your camera to focus close enough to the hole to see the inside?
At work I have a special latex goo that I pour into holes, let harden than remove. It let's me see the condition and even check the size/pitch of the threads in cases where i am missing a screw for a particular hole. Not sure what to suggest you try...