Outside of the window

" I also noticed that the left pane window, the paint is cracking. Is this also caused from moisture? "

Certainly can be and in this case most likely is.

" My question is, is this an outside caulking issue? "

Caulking is a last line of defense not primary and I doubt is the issue. 99% of the time it is an outside issue. My bet would be the head flashing/drip cap area. Can you get better pictures of the window head?

Not sure exactly where you’re specifically asking but I tried

Top of window

Got a latter out and was able to get these shots

Same are two different shots

You can see here we added in more mortar last summer when we moved in right under the overhang of the brick and even along side the brickwork to the left of the window

Left side, top of window. Window in question is facing right below this brick with the door just beyond it

I pointed to where the window is

Ladder* not latter 🤦‍♀️

Top of window

More shots of the top. I have a feeling it’s how the top of the window looks weird. I’ll attach a photo of another window and I realized it’s not like this one. It’s much cleaner.

This is another window. Different shape (slimmer) but it’s the same overall (model and make and time of install) and the top looks nice and clean

I need to look at these a little better later on but going forward, do not EVER put mortal up against the window like that. Does nothing but help rot the window. That needs to be caul with backer rod behind it.

Yeah I told my husband and he said that was from before us so looks like we got some work to do

This wall had extensive water damage prior to us moving in. Sigh. What a headache it’s been. But hoping we’re getting closer to getting it figured out. Thank you for your help. It’s much appreciated

All kinds of sources of moisture out there. Least of which (assuming it's intact and sealed to the brick) is the window. The siding and brick ledge above the window is more likely the source in my remote observation and having pulled these walls apart before.

I agree with WoW. That protruding brick ledge with the siding set on top of it is where I would be inspecting. Those brick ledges often flatten out or worse, develop a cant towards the siding.

Maybe you can try Behr waterproofer, water-based, to seal bricks above the windows from HD. It works perfect for sealing masonry. Give a try to save your headache.

Thank you!