This happens on Windows 10 but not sure this was ever a problem with older Windows versions.
I have this problem with updating taskbar icon in accordance with different state of the application. The application pulls from server what state it should be in or the application does change state by it self. This changes icon in taskbar.
I have noticed when laptop is set into sleep or hibernation and then back from sleep/hibernation for example this is happening:
Most of the time this works good but sometimes it has the tendency to stop updating icon in taskbar when debugging application the icon is changed in program like it is working normally but the icon never changes in taskbar then I tried restarting Windows Explorer in Task Manager and after restart the application icon in taskbar will have right icon.
So my guess it has something to do with Windows 10 since restarting Windows Explorer process solves this?
Here is the code that updates icon.
def update_icon(self): self.SetIcon( wx.Icon( self.empl.get_icon(get_small=False), wx.BITMAP_TYPE_ICO), self.empl.get_traybar_text())