Do I need a new window or just caulking (2nd floor window leaking on the bottom ceiling and around first floor window)

[Karyn]

I have a leak coming from the 2nd floor window that has left a long stain against where the ceiling meets the wall. It is also dripping down my first floor window. We had crazy rain last week and it also dripped down under the top part of the first floor window molding onto my blinds. It was bad.

I'm getting mixed reviews on how to fix this. Many say to just seal the outside with caulk and it will be fine. Do I need a new window? I just want to locate the reason for the leak and fix it correctly.

[Windows on Washington]

Need pictures of the outside. Most likely an issue above the window.