Thanks Dana!
We're in the midst of a monsoon so this minor issue just became major... Why would the second floor window area be leaky?
Shown here above the Liberty, missing a shutter:
Not the actual glass area, but the stone around it. Today the plaster is sloughing off the interior wall and dripping onto the steps shown here:
The front of the house was definitely repointed about 15 years ago - I assumed the rest of the house was done at the same time, but if not, is that the problem/solution?