What is making the second window not update while dragging - Pyglet

Question

I wanted to try out pyglet for making a multi-windowed app, and i got it working (sorta) My goal was to make it so you can move the windows around freely and have the squares stay still relative to the screen.

import pyglet

class window():
    def __init__(self, width, height) -> None:
        pyglet.clock.tick()
        self.screen = pyglet.window.Window(width, height)

        self.x = self.screen.get_location()[0]
        self.y = self.screen.get_location()[1]

        self.width = width
        self.height = height

        self.items = [
            pyglet.shapes.Rectangle(x=500, y=600, width=200, height=200, color=(55, 55, 255)), #square1
            pyglet.shapes.Rectangle(x=680, y=300, width=50, height=50, color=(55, 55, 255))    #square2
        ]

        @self.screen.event
        def on_draw():
            self.drawObjects()    
        
        @self.screen.event
        def on_move(x, y):
            self.x = x
            self.y = y
            self.drawObjects()
            self.screen.flip()   
            print(f"moved to {x}, {y}")    
    
    def drawObjects(self):
        self.screen.clear()
        for item in self.items:
            position = self.alignObject(item)
            pyglet.shapes.Rectangle(x=position[0], y=position[1], width=50, height=60, color=(30, 50, 70)).draw()

    def alignObject(self, object):
        return (object.x-self.x, self.screen.get_size()[1]-object.y+self.y)    

win1 = window(500, 500)
win2 = window(300, 300)

pyglet.app.run()

I think it's working how it should be position and math wise, but only win1 updates properly, win2 only updates itself after letting go. I also tried implementing a clock.schedule_interval however this only made things worse.

Has this something to do with me using the same class for both windows, or is this not how you make two windows using pyglet.

All help appreciated :)