I very often end up stripping everything surrounding windows as it's such a mixed bag depending on the building. IR stripping works but I also chip a lot of paint and loose mortar off with a chisel. Sanding seems to take forever although it feels like it should be easier.
Had a bit of a lightbulb moment. You can get some early failure of acrylics on exterior surfaces if you have a lot of fine filler dust on the surface. Happens occasionally if you go a bit overboard with the filling and sanding.
Which little greene paint did you use? It's likely moisture vapour permeable so it's possibly the paint underneath that's causing the problem.