Won't replace a missing font

Hi Illustrators!

I keep running into missing fonts on AI.

I have the text files installed on my computer- They have been able to populate in the past- however it will not let me replace the fonts now. I have tried to replace font with system and recent, does not work.

When I highlight the corrent font and click to replace- it does nothing. This is a new problem in the last few weeks- I updated the app and it did not fix the problem.