The worst offenders I've found are powershell and .Net related stuff.

You can have all the right flags enabled, then unexpectedly you'll run some commandlet and get a path too long error.

Now if your on W11/W25 and the lastest PS it might all work, but W16 and PS versions between now and then had all kinds of things pop up.

It’s not just a windows problem. File systems are an absolute disaster across all platforms. David Wheeler has a lovely article on the topic: https://dwheeler.com/essays/fixing-unix-linux-filenames.html

It’s a Windows problem. There’s still, to this day, a 259-character limit on path length in the Win32 API unless the OS has been configured to support long paths and the application uses the correct subset of Windows APIs. For example if you use ‘CreateFileA’, you’re stuck with the limit no matter what.

There’s no problem with Python in general. The registry value LongPathsEnabled, which is probably the one you were asked to set, affects the entire Windows system.

However, there’s also an older workaround that allows programs to use “extended paths” even if that setting is off, by prefixing path strings with “\\?\”. So applications using that workaround can use long paths no matter how Windows is configured. But Python doesn’t use the workaround, it uses the modern APIs and if you want long paths, you need to configure the underlying Windows system to enable it.