Why doesn't file picker on macOS show recent photos taken on an iPhone?

Super simple use case: 1. Take a picture on iPhone. 1. Go to Mac, open a program where I can choose a file to send to a friend. 1. Click on Media / Photos in the shortcuts bar. 1. Wait for it ... intended picture DOES NOT appear. Instead, I see bunch of old pictures. Why doesn't Finder's Photos integration not able to show the latest pictures I took on my iPhone? Isn't the whole idea of this that I can see what is in my Photos library? And, I have verified that the intended picture is actually showing up in Photos app, just not in the file picker in the Finder integration.