diff --git a/changelog/44736.fixed.md b/changelog/44736.fixed.md
new file mode 100644
index 00000000000..eee06decc06
--- /dev/null
+++ b/changelog/44736.fixed.md
@@ -0,0 +1,2 @@
+Commands on Windows are now prefixed with ``cmd /c`` so that compound
+commands (commands separated by ``&&``) run properly when using ``runas``
diff --git a/salt/utils/win_runas.py b/salt/utils/win_runas.py
index fc8c9c82be5..5faf01d3e80 100644
--- a/salt/utils/win_runas.py
+++ b/salt/utils/win_runas.py
@@ -187,8 +187,10 @@ def runas(cmdLine, username, password=None, cwd=None):
         | win32process.CREATE_SUSPENDED
     )
 
+    flags = win32con.STARTF_USESTDHANDLES
+    flags |= win32con.STARTF_USESHOWWINDOW
     startup_info = salt.platform.win.STARTUPINFO(
-        dwFlags=win32con.STARTF_USESTDHANDLES,
+        dwFlags=flags,
         hStdInput=stdin_read.handle,
         hStdOutput=stdout_write.handle,
         hStdError=stderr_write.handle,
@@ -204,7 +206,7 @@ def runas(cmdLine, username, password=None, cwd=None):
             int(user_token),
             logonflags=1,
             applicationname=None,
-            commandline=cmdLine,
+            commandline=f'cmd /c "{cmdLine}"',
             currentdirectory=cwd,
             creationflags=creationflags,
             startupinfo=startup_info,
@@ -286,8 +288,10 @@ def runas_unpriv(cmd, username, password, cwd=None):
     dupin = salt.platform.win.DuplicateHandle(srchandle=stdin, inherit=True)
 
     # Get startup info structure
+    flags = win32con.STARTF_USESTDHANDLES
+    flags |= win32con.STARTF_USESHOWWINDOW
     startup_info = salt.platform.win.STARTUPINFO(
-        dwFlags=win32con.STARTF_USESTDHANDLES,
+        dwFlags=flags,
         hStdInput=dupin,
         hStdOutput=c2pwrite,
         hStdError=errwrite,
@@ -300,7 +304,7 @@ def runas_unpriv(cmd, username, password, cwd=None):
             domain=domain,
             password=password,
             logonflags=salt.platform.win.LOGON_WITH_PROFILE,
-            commandline=cmd,
+            commandline=f'cmd /c "{cmd}"',
             startupinfo=startup_info,
             currentdirectory=cwd,
         )
diff --git a/tests/pytests/functional/utils/test_win_runas.py b/tests/pytests/functional/utils/test_win_runas.py
new file mode 100644
index 00000000000..e6f06d6948c
--- /dev/null
+++ b/tests/pytests/functional/utils/test_win_runas.py
@@ -0,0 +1,38 @@
+"""
+Test the win_runas util
+"""
+
+import pytest
+
+import salt.utils.win_runas as win_runas
+
+pytestmark = [
+    pytest.mark.windows_whitelisted,
+    pytest.mark.skip_unless_on_windows,
+]
+
+
+@pytest.fixture
+def user():
+    with pytest.helpers.create_account() as account:
+        yield account
+
+
+def test_runas(user):
+    cmd = "hostname && echo foo"
+    result = win_runas.runas(
+        cmdLine=cmd,
+        username=user.username,
+        password=user.password,
+    )
+    assert "foo" in result["stdout"]
+
+
+def test_runas_unpriv(user):
+    cmd = "hostname && echo foo"
+    result = win_runas.runas_unpriv(
+        cmd=cmd,
+        username=user.username,
+        password=user.password,
+    )
+    assert "foo" in result["stdout"]
diff --git a/tests/support/pytest/helpers.py b/tests/support/pytest/helpers.py
index 8766607a49f..78de282ba95 100644
--- a/tests/support/pytest/helpers.py
+++ b/tests/support/pytest/helpers.py
@@ -332,8 +332,9 @@ class TestAccount:
         if salt.utils.platform.is_windows():
             log.debug("Configuring system account: %s", self)
             ret = self.sminion.functions.user.update(
-                self.username, password_never_expires=True
+                self.username, expired=False, password_never_expires=True
             )
+            assert ret is True
         if salt.utils.platform.is_darwin() or salt.utils.platform.is_windows():
             password = self.password
         else: