This needs to be addressed in list2cmdline to be consistent with how POSIX converts every element of args via PyUnicode_FSConverter. For example:

if isinstance(args, bytes):
    args = os.fsdecode(args)
elif isinstance(args, os.PathLike):
    if shell:
        raise ValueError('PathLike args is not allowed when '
                         'shell is true.')
    else:
        args = [args]

if not isinstance(args, str):
    args = list2cmdline(args)

if executable is not None:
    executable = os.fsdecode(executable)

Then in list2cmdline, decode the items via os.fsdecode :

for arg in seq:
    if not isinstance(arg, str):
        arg = os.fsdecode(arg)

This does look like it would be nicer, allowing more mixing and matching of types.

@eryksun 's comment is related to the old version of the PR. I addressed it, except that that I decided to reject bytes args on Windows with shell=True as it is ambiguous and is not actually needed. It is enough to have a difference in interpreting str args.

I still think bytes and pathlike should be supported for every item of args. The POSIX implementation doesn't limit this to args[0] (though not documented), and I think that's proper. A script shouldn't have to special-case calling os.fsdecode for a pathlike argument. That's inefficient for POSIX, for which os.fsencode would be better. While os.fspath would be efficient, it's insufficient because it might return bytes on Windows.

The POSIX implementation accepts also bytes as args and as any item of args. If allow path-like arguments, we should consider also adding support of bytes arguments and program name.

The elif chain could be simplified to have less repeated code:

elif isinstance(args, (bytes, os.PathLike)):
    if shell:
        raise TypeError(f'{type(args)} args not allowed when shell=True on Windows')`
    args = list2cmdline([args])

Error messages should be different. Path-like args is not allowed on all platforms, bytes args is not allowed only on Windows.

for consistency of error messages with my suggestion above I think TypeError(f'{type(args)} args is not allowed when ' ...). It is good for that to render as <class os.PathLike> as that is less confusing to the error message reader than "path-like" which they might be more likely to mis-interpret in English as suggesting anything that looks like a path within a string.

I like to make the first line descriptive comment a docstring. it shows up nicely in verbose testing mode.

FYI - these 3.6 and 3.7 versionchanged updates should be made to the docs today to clarify the existing behavior on their own (and backported to at least the 3.7 docs)

This does look like it would be nicer, allowing more mixing and matching of types.