Terry J. Reedy <tjre...@udel.edu> added the comment:

Looking at the animated .gif, Jim's problem has nothing to do with IDLE in 
particular, and is as least partly specific to his system, as I do not have the 
same problem on my system.  (That does not mean that improvements are not 
possible, so that reboots are not needed after updates.)

If one runs a file with python.exe that does not exit immediately, the taskbar 
icon is the 'Python Console icon, a dark console with blue title bar and text 
and the Python double snake overlaid.  If on runs a file with pythonw.exe (no 
console) that does not exit immediately, the taskbar icon should be the 'Python 
GUI' icon, a spiral-bound notebook page with folded upper right corner and the 
Python double snake overlaid.  The expected use case is a GUI program, such as 
a tkinter program, that runs an event loop until closed.  IDLE is just the 
prime example of such. Another example is the test program for this issue.

import tkinter as tk
r = tk.Tk()
r.mainloop()

When I name this file tem.py or tem.pyw and double-click, I get the respective 
Python icons.

Jim, the 'blank' icon you see when you double-click *.pyw is a white sheet of 
paper with the upper right corner folded.  It is the first one shown when the 
builtin icons are displayed.  It is used when Windows cannot find the proper 
icon for an application (or perhaps also when there is None).

Some while ago, after an update, my pinned Skype icon visually changed from the 
blue blob with white S to this default.  Yesterday, I right-clicked the folded 
page icon, right-clicked 'Skype, selected Properties, and then [Change Icon] on 
the Shortcut tab.

An error box popped up with a message similar to 
"%SystemRoot%\Installer\{3B7E914A-93D5-4A29-92BB-AF8C3F66C431}\SkypeIcon.exe 
cannot be found". My guess is that an update changed the uuid without updating 
the pinned icon, so the default folded page is the substitute.  When I clicked 
'OK', the Change Icon dialog appeared.  When I browsed to the Skype directory, 
I did not find an icon file, so I clicked on Skype.exe instead, and that 
worked, and I again have the Skype icon on my taskbar.

Jim, I suggest you try the same, except navigate to 3.6 pythonw.exe.  Running 
'import sys; sys.executable' shows the location.  If pythonw.exe has the proper 
icon, I expect that this should work.

----------
type: enhancement -> behavior
versions: +Python 3.6 -Python 3.8

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue32611>
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