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Thanks for reporting this! It was an interesting rabbit hole to follow while trying to figure out what's going on :)
It turns out that Windows handles ANSI escape sequences differently than Linux or Mac. For a long time, it didn't support them at all, and apparently with the new "Windows Terminal" app or PowerShell, they should be supported now (https://en.wikipedia.org/wiki/ANSI_escape_code#DOS,_OS/2,_and_Windows).
However, click uses colorama, and colorama has some custom API calls to print colors in Windows terminal. At the same time, it strips the ANSI escape codes. So while running the uptimer from this chapter in the terminal prints colors correctly, tests are failing because they expect the ANSI escape characters.
There is a pending PR to colorama to change this behavior, but it's still open since 2016, so I don't think it will be implemented anytime soon.
When I run the ch11 tests I seem to get an error with the click style related tests. Do you think is powershell related?
Windows 10
Python 3.8.5
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