diff --git a/salt/modules/cmdmod.py b/salt/modules/cmdmod.py
index 6fdd53d5e789..a255820da147 100644
--- a/salt/modules/cmdmod.py
+++ b/salt/modules/cmdmod.py
@@ -55,6 +55,7 @@
 if salt.utils.platform.is_windows():
     import salt.platform.win
     from salt.utils.win_functions import escape_argument as _cmd_quote
+    from salt.utils.win_functions import shlex_split
     from salt.utils.win_runas import runas as win_runas
 
     HAS_WIN_RUNAS = True
@@ -100,25 +101,20 @@ def _check_cb(cb_):
     return lambda x: x
 
 
-def _python_shell_default(python_shell, shell=False):
+def _python_shell_default(python_shell, __pub_jid):
     """
     Set python_shell default based on the shell parameter and __opts__['cmd_safe']
     """
-    if shell:
-        if salt.utils.platform.is_windows():
-            # On Windows python_shell / subprocess 'shell' parameter must always be
-            # False as we prepend the shell manually
-            return False
-        else:
-            # Non-Windows requires python_shell to be enabled
-            return True if python_shell is None else python_shell
-    else:
-        try:
-            if __opts__.get("cmd_safe", True) is False and python_shell is None:
-                # Override-switch for python_shell
-                return True
-        except NameError:
-            pass
+    try:
+        # Default to python_shell=True when run directly from remote execution
+        # system. Cross-module calls won't have a jid.
+        if __pub_jid and python_shell is None:
+            return True
+        elif __opts__.get("cmd_safe", True) is False and python_shell is None:
+            # Override-switch for python_shell
+            return True
+    except NameError:
+        pass
     return python_shell
 
 
@@ -305,7 +301,7 @@ def _run(
     log_callback=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=False,
     env=None,
     clean_env=False,
@@ -973,7 +969,7 @@ def _run_quiet(
     stdin=None,
     output_encoding=None,
     runas=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=False,
     env=None,
     template=None,
@@ -1022,7 +1018,7 @@ def _run_all_quiet(
     cwd=None,
     stdin=None,
     runas=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=False,
     env=None,
     template=None,
@@ -1078,7 +1074,7 @@ def run(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     clean_env=False,
@@ -1346,7 +1342,7 @@ def run(
 
         salt '*' cmd.run cmd='sed -e s/=/:/g'
     """
-    python_shell = _python_shell_default(python_shell, shell)
+    python_shell = _python_shell_default(python_shell, kwargs.get("__pub_jid", ""))
     stderr = subprocess.STDOUT if redirect_stderr else subprocess.PIPE
     ret = _run(
         cmd,
@@ -1671,7 +1667,7 @@ def run_stdout(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     clean_env=False,
@@ -1866,7 +1862,7 @@ def run_stdout(
 
         salt '*' cmd.run_stdout "grep f" stdin='one\\ntwo\\nthree\\nfour\\nfive\\n'
     """
-    python_shell = _python_shell_default(python_shell, shell)
+    python_shell = _python_shell_default(python_shell, kwargs.get("__pub_jid", ""))
     ret = _run(
         cmd,
         runas=runas,
@@ -1905,7 +1901,7 @@ def run_stderr(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     clean_env=False,
@@ -2100,7 +2096,7 @@ def run_stderr(
 
         salt '*' cmd.run_stderr "grep f" stdin='one\\ntwo\\nthree\\nfour\\nfive\\n'
     """
-    python_shell = _python_shell_default(python_shell, shell)
+    python_shell = _python_shell_default(python_shell, kwargs.get("__pub_jid", ""))
     ret = _run(
         cmd,
         runas=runas,
@@ -2139,7 +2135,7 @@ def run_all(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     clean_env=False,
@@ -2377,7 +2373,7 @@ def run_all(
 
         salt '*' cmd.run_all "grep f" stdin='one\\ntwo\\nthree\\nfour\\nfive\\n'
     """
-    python_shell = _python_shell_default(python_shell, shell)
+    python_shell = _python_shell_default(python_shell, kwargs.get("__pub_jid", ""))
     stderr = subprocess.STDOUT if redirect_stderr else subprocess.PIPE
     ret = _run(
         cmd,
@@ -2421,7 +2417,7 @@ def retcode(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     clean_env=False,
@@ -2602,7 +2598,7 @@ def retcode(
 
         salt '*' cmd.retcode "grep f" stdin='one\\ntwo\\nthree\\nfour\\nfive\\n'
     """
-    python_shell = _python_shell_default(python_shell, shell)
+    python_shell = _python_shell_default(python_shell, kwargs.get("__pub_jid", ""))
     ret = _run(
         cmd,
         runas=runas,
@@ -2639,7 +2635,7 @@ def _retcode_quiet(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=False,
     env=None,
     clean_env=False,
@@ -2697,7 +2693,7 @@ def script(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     template=None,
@@ -2903,7 +2899,8 @@ def script(
             saltenv = __opts__.get("saltenv", "base")
         except NameError:
             saltenv = "base"
-    python_shell = _python_shell_default(python_shell, shell)
+
+    python_shell = _python_shell_default(python_shell, kwargs.get("__pub_jid", ""))
 
     def _cleanup_tempfile(path):
         try:
@@ -2995,10 +2992,13 @@ def _cleanup_tempfile(path):
         os.chmod(path, 320)
         os.chown(path, __salt__["file.user_to_uid"](runas), -1)
 
-    if isinstance(args, (list, tuple)):
-        new_cmd = [path, *args] if args else [path]
-    else:
-        new_cmd = [path, str(args)] if args else [path]
+    if isinstance(args, str):
+        if salt.utils.platform.is_windows():
+            args = shlex_split(args)
+        else:
+            args = shlex.split(args)
+
+    new_cmd = [path, *args] if args else [path]
 
     ret = {}
     try:
@@ -3050,7 +3050,7 @@ def script_retcode(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     template="jinja",
@@ -3395,7 +3395,7 @@ def run_chroot(
     stdin=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=True,
     binds=None,
     env=None,
@@ -4627,7 +4627,7 @@ def run_bg(
     cwd=None,
     runas=None,
     group=None,
-    shell=None,
+    shell=DEFAULT_SHELL,
     python_shell=None,
     env=None,
     clean_env=False,
@@ -4832,7 +4832,7 @@ def run_bg(
 
         salt '*' cmd.run_bg cmd='ls -lR / | sed -e s/=/:/g > /tmp/dontwait'
     """
-    python_shell = _python_shell_default(python_shell, shell)
+    python_shell = _python_shell_default(python_shell, kwargs.get("__pub_jid", ""))
     res = _run(
         cmd,
         stdin=None,
diff --git a/salt/utils/win_functions.py b/salt/utils/win_functions.py
index 24c319749f82..eb13f357b27d 100644
--- a/salt/utils/win_functions.py
+++ b/salt/utils/win_functions.py
@@ -421,3 +421,41 @@ def squid_to_guid(squid):
             guid += squid_match.group(index)[::-1]
         guid += "}"
     return guid
+
+
+def shlex_split(string):
+    """
+    Windows version of shlex.split()
+
+    Based on winshlex: https://github.com/jdjebi/winshlex/blob/master/winshlex/lex.py
+    """
+    re_cmd_lex = r""""((?:""|\\["\\]|[^"])*)"?()|(\\\\(?=\\*")|\\")|(&&?|\|\|?|\d?>|[<])|([^\s"&|<>]+)|(\s+)|(.)"""
+    args = []
+    accu = None  # collects pieces of one arg
+    for qs, qss, esc, pipe, word, white, fail in re.findall(re_cmd_lex, string):
+        if word:
+            pass  # most frequent
+        elif esc:
+            word = esc[1]
+        elif white or pipe:
+            if accu is not None:
+                args.append(accu)
+            if pipe:
+                args.append(pipe)
+            accu = None
+            continue
+        elif fail:
+            raise ValueError("invalid or incomplete shell string")
+        elif qs:
+            word = qs.replace('\\"', '"').replace("\\\\", "\\")
+            if platform == 0:
+                word = word.replace('""', '"')
+        else:
+            word = qss  # may be even empty; must be last
+
+        accu = (accu or "") + word
+
+    if accu is not None:
+        args.append(accu)
+
+    return args
diff --git a/tests/integration/modules/test_cmdmod.py b/tests/integration/modules/test_cmdmod.py
index 7a965e9fe4e8..5ee6be9075d1 100644
--- a/tests/integration/modules/test_cmdmod.py
+++ b/tests/integration/modules/test_cmdmod.py
@@ -293,6 +293,7 @@ def test_script_cwd_with_space(self):
         )
         self.assertEqual(ret["stdout"], " ".join(args))
 
+    @pytest.mark.skip_if_not_root
     @pytest.mark.destructive_test
     def test_tty(self):
         """
diff --git a/tests/integration/shell/test_enabled.py b/tests/integration/shell/test_enabled.py
index 5adcc89a247d..146e74f9746b 100644
--- a/tests/integration/shell/test_enabled.py
+++ b/tests/integration/shell/test_enabled.py
@@ -23,26 +23,26 @@ class EnabledTest(ModuleCase):
     )
 
     @pytest.mark.skip_on_windows(reason="Skip on Windows OS")
-    def test_shell_default_disabled(self):
+    @pytest.mark.skip_on_freebsd
+    def test_shell_default_enabled(self):
         """
-        ensure that python_shell defaults to False for cmd.run
+        ensure that python_shell defaults to True for cmd.run
         """
-        disabled_ret = (
-            "first\nsecond\nthird\n|\nwc\n-l\n;\nexport\nSALTY_VARIABLE=saltines"
-            "\n&&\necho\n$SALTY_VARIABLE\n;\necho\nduh\n&>\n/dev/null"
-        )
+        disabled_ret = "3\nsaltines"  # the result of running self.cmd in a shell
         ret = self.run_function("cmd.run", [self.cmd])
         self.assertEqual(ret, disabled_ret)
 
     @pytest.mark.skip_on_windows(reason="Skip on Windows OS")
-    @pytest.mark.skip_on_freebsd
-    def test_shell_enabled(self):
+    def test_shell_disabled(self):
         """
-        test shell enabled output for cmd.run
+        test shell disabled output for cmd.run
         """
-        enabled_ret = "3\nsaltines"  # the result of running self.cmd in a shell
-        ret = self.run_function("cmd.run", [self.cmd], python_shell=True)
-        self.assertEqual(ret.strip(), enabled_ret)
+        disabled_ret = (
+            "first\nsecond\nthird\n|\nwc\n-l\n;\nexport\nSALTY_VARIABLE=saltines"
+            "\n&&\necho\n$SALTY_VARIABLE\n;\necho\nduh\n&>\n/dev/null"
+        )
+        ret = self.run_function("cmd.run", [self.cmd], python_shell=False)
+        self.assertEqual(ret.strip(), disabled_ret)
 
     @pytest.mark.skip_on_windows(reason="Skip on Windows OS")
     @pytest.mark.skip_on_freebsd
diff --git a/tests/pytests/functional/modules/cmd/test_script_batch.py b/tests/pytests/functional/modules/cmd/test_script_batch.py
index 0184aace200c..721505f78670 100644
--- a/tests/pytests/functional/modules/cmd/test_script_batch.py
+++ b/tests/pytests/functional/modules/cmd/test_script_batch.py
@@ -27,36 +27,40 @@ def echo_script(state_tree):
 
 
 @pytest.mark.parametrize(
-    "command, expected",
+    "args, expected",
     [
+        ("foo bar", "a: foo, b: bar"),
+        ('foo "bar bar"', "a: foo, b: bar bar"),
         (["foo", "bar"], "a: foo, b: bar"),
         (["foo foo", "bar bar"], "a: foo foo, b: bar bar"),
     ],
 )
-def test_echo(modules, echo_script, command, expected):
+def test_echo(modules, echo_script, args, expected):
     """
     Test argument processing with a batch script
     """
     script = "salt://echo-script/test.bat"
-    result = modules.cmd.script(script, args=command, shell="cmd")
+    result = modules.cmd.script(script, args=args, shell="cmd")
     assert result["stdout"] == expected
 
 
 @pytest.mark.parametrize(
-    "command, expected",
+    "args, expected",
     [
+        ("foo bar", "a: foo, b: bar"),
+        ('foo "bar bar"', "a: foo, b: bar bar"),
         (["foo", "bar"], "a: foo, b: bar"),
         (["foo foo", "bar bar"], "a: foo foo, b: bar bar"),
     ],
 )
-def test_echo_runas(modules, account, echo_script, command, expected):
+def test_echo_runas(modules, account, echo_script, args, expected):
     """
     Test argument processing with a batch script and runas
     """
     script = "salt://echo-script/test.bat"
     result = modules.cmd.script(
         script,
-        args=command,
+        args=args,
         shell="cmd",
         runas=account.username,
         password=account.password,
diff --git a/tests/pytests/functional/modules/cmd/test_script_powershell.py b/tests/pytests/functional/modules/cmd/test_script_powershell.py
index c1f076dca8a7..7618e28c5900 100644
--- a/tests/pytests/functional/modules/cmd/test_script_powershell.py
+++ b/tests/pytests/functional/modules/cmd/test_script_powershell.py
@@ -63,17 +63,19 @@ def test_exitcode(cmd, shell, exitcode_script):
 
 
 @pytest.mark.parametrize(
-    "command, expected",
+    "args, expected",
     [
+        ("foo bar", "a: foo, b: bar"),
+        ('foo "bar bar"', "a: foo, b: bar bar"),
         (["foo", "bar"], "a: foo, b: bar"),
         (["foo foo", "bar bar"], "a: foo foo, b: bar bar"),
     ],
 )
-def test_echo(cmd, shell, echo_script, command, expected):
+def test_echo(cmd, shell, echo_script, args, expected):
     """
     Test argument processing with a powershell script
     """
-    ret = cmd.script("salt://echo.ps1", args=command, shell=shell, saltenv="base")
+    ret = cmd.script("salt://echo.ps1", args=args, shell=shell, saltenv="base")
     assert isinstance(ret["pid"], int)
     assert ret["retcode"] == 0
     assert ret["stderr"] == ""
@@ -81,19 +83,21 @@ def test_echo(cmd, shell, echo_script, command, expected):
 
 
 @pytest.mark.parametrize(
-    "command, expected",
+    "args, expected",
     [
+        ("foo bar", "a: foo, b: bar"),
+        ('foo "bar bar"', "a: foo, b: bar bar"),
         (["foo", "bar"], "a: foo, b: bar"),
         (["foo foo", "bar bar"], "a: foo foo, b: bar bar"),
     ],
 )
-def test_echo_runas(cmd, shell, account, echo_script, command, expected):
+def test_echo_runas(cmd, shell, account, echo_script, args, expected):
     """
     Test argument processing with a powershell script and runas
     """
     ret = cmd.script(
         "salt://echo.ps1",
-        args=command,
+        args=args,
         shell=shell,
         runas=account.username,
         password=account.password,
diff --git a/tests/pytests/unit/modules/test_cmdmod.py b/tests/pytests/unit/modules/test_cmdmod.py
index dccb23f0de67..92ea89965b2f 100644
--- a/tests/pytests/unit/modules/test_cmdmod.py
+++ b/tests/pytests/unit/modules/test_cmdmod.py
@@ -17,6 +17,7 @@
 import salt.grains.extra
 import salt.modules.cmdmod as cmdmod
 import salt.utils.files
+import salt.utils.path
 import salt.utils.platform
 import salt.utils.stringutils
 from salt._logging import LOG_LEVELS
@@ -670,12 +671,17 @@ def test_run_all_output_loglevel_debug(caplog):
     stdout = b"test"
     proc = MagicMock(return_value=MockTimedProc(stdout=stdout))
 
-    expected = "Executing command 'some' in directory"
+    if salt.utils.platform.is_windows():
+        run_cmd = salt.utils.path.which("cmd")
+        expected = f"Executing command '{run_cmd}' in directory"
+    else:
+        expected = "Executing command 'some' in directory"
+
     with patch("salt.utils.timed_subprocess.TimedProc", proc):
         with caplog.at_level(logging.DEBUG, logger="salt.modules.cmdmod"):
             ret = cmdmod.run_all("some command", output_loglevel="debug")
         result = caplog.text
-        assert expected in result
+        assert expected.lower() in result.lower()
 
     assert ret["stdout"] == salt.utils.stringutils.to_unicode(stdout)
 
diff --git a/tests/pytests/unit/utils/test_win_functions.py b/tests/pytests/unit/utils/test_win_functions.py
index 6fcb1081d38d..d79d52f0921f 100644
--- a/tests/pytests/unit/utils/test_win_functions.py
+++ b/tests/pytests/unit/utils/test_win_functions.py
@@ -190,3 +190,19 @@ def test_get_sam_name(test_user):
     expected = "\\".join([platform.node()[:15], test_user])
     result = win_functions.get_sam_name(test_user)
     assert result.lower() == expected.lower()
+
+
+@pytest.mark.parametrize(
+    "string, expected",
+    [
+        ("foo", ["foo"]),
+        ("foo bar", ["foo", "bar"]),
+        ("foo bar=baz", ["foo", "bar=baz"]),
+        ('foo "bar baz"', ["foo", "bar baz"]),
+        ("C:\\Temp\\test.txt", ["C:\\Temp\\test.txt"]),
+        ('"C:\\Temp\\Space Dir\\test.txt"', ["C:\\Temp\\Space Dir\\test.txt"]),
+    ],
+)
+def test_shlex_split(string, expected):
+    result = win_functions.shlex_split(string=string)
+    assert result == expected