diff --git a/src/manage/scriptutils.py b/src/manage/scriptutils.py
index d4b9715..07e4a11 100644
--- a/src/manage/scriptutils.py
+++ b/src/manage/scriptutils.py
@@ -19,11 +19,16 @@ def _find_shebang_command(cmd, full_cmd):
     if not sh_cmd.match("*.exe"):
         sh_cmd = sh_cmd.with_name(sh_cmd.name + ".exe")
 
-    is_default = sh_cmd.match("python.exe") or sh_cmd.match("py.exe")
+    is_wdefault = sh_cmd.match("pythonw.exe") or sh_cmd.match("pyw.exe")
+    is_default = is_wdefault or sh_cmd.match("python.exe") or sh_cmd.match("py.exe")
 
     for i in cmd.get_installs():
         if is_default and i.get("default"):
-            return i
+            if is_wdefault:
+                target = [t for t in i.get("run-for", []) if t.get("windowed")]
+                if target:
+                    return {**i, "executable": i["prefix"] / target[0]["target"]}
+            return {**i, "executable": i["prefix"] / i["executable"]}
         for a in i.get("alias", ()):
             if sh_cmd.match(a["name"]):
                 LOGGER.debug("Matched alias %s in %s", a["name"], i["id"])
@@ -35,7 +40,10 @@ def _find_shebang_command(cmd, full_cmd):
             LOGGER.debug("Matched executable %s in %s", i["executable"], i["id"])
             return i
 
-    # Fallback search for 'python<TAG>.exe' shebangs
+    # Fallback search for 'python[w]<TAG>.exe' shebangs
+    if sh_cmd.match("pythonw*.exe"):
+        tag = sh_cmd.name[7:-4]
+        return cmd.get_install_to_run(f"PythonCore/{tag}", windowed=True)
     if sh_cmd.match("python*.exe"):
         tag = sh_cmd.name[6:-4]
         return cmd.get_install_to_run(f"PythonCore/{tag}")
diff --git a/tests/conftest.py b/tests/conftest.py
index 41957ca..6faf08e 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -159,7 +159,14 @@ def __init__(self, global_dir, installs=[]):
     def get_installs(self, *, include_unmanaged=True, set_default=True):
         return self.installs
 
-    def get_install_to_run(self, tag):
+    def get_install_to_run(self, tag, *, windowed=False):
+        if windowed:
+            i = self.get_install_to_run(tag)
+            target = [t for t in i.get("run-for", []) if t.get("windowed")]
+            if target:
+                return {**i, "executable": i["prefix"] / target[0]["target"]}
+            return i
+
         company, _, tag = tag.replace("/", "\\").rpartition("\\")
         return [i for i in self.installs
                 if i["tag"] == tag and (not company or i["company"] == company)][0]
diff --git a/tests/test_scriptutils.py b/tests/test_scriptutils.py
index 05d3309..0ee8804 100644
--- a/tests/test_scriptutils.py
+++ b/tests/test_scriptutils.py
@@ -8,6 +8,7 @@
 
 from manage.scriptutils import (
     find_install_from_script,
+    _find_shebang_command,
     _read_script,
     NewEncoding,
     _maybe_quote,
@@ -69,6 +70,25 @@ def test_read_shebang(fake_config, tmp_path, script, expect):
         assert not expect
 
 
+def test_default_py_shebang(fake_config, tmp_path):
+    inst = _fake_install("1.0", company="PythonCore", prefix=PurePath("C:\\TestRoot"), default=True)
+    inst["run-for"] = [
+        dict(name="python.exe", target=".\\python.exe"),
+        dict(name="pythonw.exe", target=".\\pythonw.exe", windowed=1),
+    ]
+    fake_config.installs[:] = [inst]
+
+    # Finds the install's default executable
+    assert _find_shebang_command(fake_config, "python")["executable"].match("test-binary-1.0.exe")
+    assert _find_shebang_command(fake_config, "py")["executable"].match("test-binary-1.0.exe")
+    assert _find_shebang_command(fake_config, "python1.0")["executable"].match("test-binary-1.0.exe")
+    # Finds the install's run-for executable with windowed=1
+    assert _find_shebang_command(fake_config, "pythonw")["executable"].match("pythonw.exe")
+    assert _find_shebang_command(fake_config, "pyw")["executable"].match("pythonw.exe")
+    assert _find_shebang_command(fake_config, "pythonw1.0")["executable"].match("pythonw.exe")
+
+
+
 @pytest.mark.parametrize("script, expect", [
     ("# not a coding comment", None),
     ("# coding: utf-8-sig", None),