Does aksokcancel return "true" or True ?  The docstring should say True   This is pervasive throughout the module.  tkinter has such a mishmash of numbers supplied as strings, strings supplied as constants making this carelessness egregious.  On the topic of constants, the messagebox module redefines OK.  You might argue that the definition didn't change.  I suspect this issue applies to all versions of tkinter or Tkinter having the messagebox.

# types
ABORTRETRYIGNORE = "abortretryignore"
OK = "ok"
...

# replies
...
OK = "ok"



def askokcancel(title=None, message=None, **options):
    "Ask if operation should proceed; return true if the answer is ok"
    s = _show(title, message, QUESTION, OKCANCEL, **options)
    return s == OK

Please note that calling something "sloppy" and that somehow its development was done in some "carelessness" fashion to the point of being "egregious" is not motivating to others to try and help. Trying to support all of this code for free in one's spare time is not easy, so I would ask you try to be more understanding and nicer in your comments.

Sometimes I say nice things about python.

https://www.quora.com/Is-Python-fast-yet/answer/David-Lambert-86?__nsrc__=4&__snid3__=6376944631

On 10/31/19 1:14 PM, Brett Cannon wrote:
> Brett Cannon <brett@python.org> added the comment:
>
> Please note that calling something "sloppy" and that somehow its development was done in some "carelessness" fashion to the point of being "egregious" is not motivating to others to try and help. Trying to support all of this code for free in one's spare time is not easy, so I would ask you try to be more understanding and nicer in your comments.
>
> ----------
> nosy: +brett.cannon
>
> _______________________________________
> Python tracker <report@bugs.python.org>
> <https://bugs.python.org/issue38649>
> _______________________________________

I agree that there is a problem. tkinter.messagebox is poorly documented. Different functions can return True, False, None or the name of the button, and it is not specified which function what returns. Set of acceptable values for type and icon are not documented. And there are no tests, so we cannot be sure that all works as expected on all platforms.

I am working on it.