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Insulating window weight pockets.
It may be be covered with lath and plaster as well which would open up another can of worms.
Cut strips of foil faced rigid foam insulation to fit into the weight pockets.
Then cut strips of 2 foam board to fit into the wieght pocket where the weights used to be.
I did this on several windows.
For window weight pockets i just blow out as much dust as possible then spray the area with water then canned foam the cavity.
If there is a gap i would caulk it.
Remove sash weights for upper sash the ones closest to exterior wall and replace pulleys with the pullman device that fits into the pulley hole.
Stack strips to completely fill the void.
Check the fit of the brick molding.
That will address any issues with the weight pockets.
Use foil tape to seal the joint between the window jamb and foam insulation.
These houses typically have no water management details around windows doors which works while the wall is open but will cause issues with insulation.
Remove exterior flat casing to reveal weight pocket.
Use a hammer and pry bar to carefully remove the wood trim from around the inside of the window exposing the sash weight pockets.
I restore these windows for a living.
This old house general contractor tom silva shows an energy efficient way to insulate old windows.