Roof Leak : HomeImprovement

I have a leak that started in February after a rain/freezing rain storm here in Illinois. I have already posted this (Previous Post), but I have more info. The leak is next to my front door. Here it is leaking. Leak. Here is the front of my house Front of House. I went on the roof with a hose and sprayed this area I have circled Front of House Leak Area and it did leak. I then took some caulk and put it in that area Caulked Area. Yesterday we got a bunch of rain and the leak is still there. I went out while it was raining and pulled it open to take a picture from below: View From Below. Any ideas on how I can fix this? I thought about maybe caulking these areas Caulk . Any other ideas would be appreciated.

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