Windows leaking from top

[Nicole A.]

Every time it rains, there are two windows that leak from the top side in one of our properties. These windows are right above each other--a window in a bedroom on 1st and 2nd floor units.

First, we change the roof because there was other ceiling water damage. That seems to fix that issue. But then the next rain, I get a text about these windows leaking.

Then, we recaulk all of the windows' exterior. Nope! Still leaks!

Last Sunday, my husband and I go there and he sprays the building with a water hose and I wait inside and watch for it to start leaking. He finds a big enough hole in the bricking that he fills and adds caulk to one of the windows. The next day/yesterday, we have a pretty good rain come through.

STILL LEAKING!! And this was a really heavy, long rain, so it actually seemed to leak worse and even stained the ceiling right in front of the window. My guess is the water is running along the frame/studs/whatever and getting to that drywall.

When inside, and you look up at the top of the window frame itself, the water is just seeping/dripping through. We are pretty confident it's not the roof being that the roof is brand new and we did a hose test on the roof with no dripping.

All that can be left is that all of the brick on that side of the building needs to be repointed and we're just going to completely replace those two windows. I'm just so frustrated. 

Anyone ever experience similar?