I can reproduce that test failure with Tk 8.6.10 on macOS, along with a few others. I believe various small things have changed in Tk somewhere between 8.6.8 and 8.6.10 in ways that affect some of the Python Tk gui tests, like test_tk and test_ttk_guionly. Some of our tests are pretty brittle with regard to Tk behavior; they captured how a particular version of Tk worked without necessarily a guarantee on the Tk side that the observed behavior wouldn't change. Someone needs to go through and make the tests work with all recent versions of Tk 8.6.x and someone should also get at least some buildbots running with 8.6.10 and really running the gui tests.