diff --git a/custom_components/pyscript/__init__.py b/custom_components/pyscript/__init__.py
index b602ebe..8dcb7f5 100644
--- a/custom_components/pyscript/__init__.py
+++ b/custom_components/pyscript/__init__.py
@@ -11,6 +11,7 @@
 import shutil
 import time
 import traceback
+from types import ModuleType
 from typing import Any
 
 import voluptuous as vol
@@ -74,6 +75,16 @@
 CONFIG_SCHEMA = vol.Schema({DOMAIN: PYSCRIPT_SCHEMA}, extra=vol.ALLOW_EXTRA)
 
 
+def _relative_script_path(path: str, root: str, path_module: ModuleType = os.path) -> str:
+    """Return a slash-separated path relative to the pyscript root."""
+    return path_module.relpath(path, root).replace(path_module.sep, "/")
+
+
+def _is_requirements_file(path: str, path_module: ModuleType = os.path) -> bool:
+    """Match a requirements file using the host path rules."""
+    return path_module.basename(path) == REQUIREMENTS_FILE
+
+
 async def async_setup(hass: HomeAssistant, config: ConfigType) -> bool:
     """Component setup, run import config flow for each entry in config."""
     await restore_state(hass)
@@ -225,9 +236,11 @@ def check_event(event: FileSystemEvent, do_reload: bool) -> bool:
             # also check dest_path: atomic saves (tempfile + os.replace) surface
             # as a moved event whose src_path is an unrelated temp name
             paths = (event.src_path, event.dest_path)
-            for valid_suffix in [".py", ".yaml", "/" + REQUIREMENTS_FILE]:
+            for valid_suffix in [".py", ".yaml"]:
                 if any(path.endswith(valid_suffix) for path in paths):
                     return True
+            if any(_is_requirements_file(path) for path in paths):
+                return True
             return do_reload
 
         while True:
@@ -533,11 +546,11 @@ def glob_read_files(
         for path, match, check_config, autoload in load_paths:
             for this_path in sorted(glob.glob(os.path.join(pyscript_dir, path, match), recursive=True)):
                 rel_import_path = None
-                rel_path = this_path
-                if rel_path.startswith(pyscript_dir):
-                    rel_path = rel_path[len(pyscript_dir) :]
-                if rel_path.startswith("/"):
-                    rel_path = rel_path[1:]
+                try:
+                    rel_path = _relative_script_path(this_path, pyscript_dir)
+                except ValueError as exc:
+                    _LOGGER.error("load_scripts: skipping %s due to exception %s", this_path, exc)
+                    continue
                 if rel_path[0] == "#" or rel_path.find("/#") >= 0:
                     # skip "commented" files and directories
                     continue
diff --git a/tests/test_decorator_errors.py b/tests/test_decorator_errors.py
index 94879ae..dbb38da 100644
--- a/tests/test_decorator_errors.py
+++ b/tests/test_decorator_errors.py
@@ -25,6 +25,9 @@ async def setup_script(hass, notify_q, now, source):
     with (
         patch("custom_components.pyscript.os.path.isdir", return_value=True),
         patch("custom_components.pyscript.glob.iglob", return_value=scripts),
+        # This fixture deliberately uses a synthetic /hello.py for stable
+        # traceback assertions; emulate the relative name of an in-root file.
+        patch("custom_components.pyscript._relative_script_path", return_value="hello.py"),
         patch("custom_components.pyscript.global_ctx.open", mock_open(read_data=source)),
         patch("custom_components.pyscript.trigger.dt_now", return_value=now),
         patch("homeassistant.config.load_yaml_config_file", return_value={}),
diff --git a/tests/test_init.py b/tests/test_init.py
index 98cd0ac..eb17d2d 100644
--- a/tests/test_init.py
+++ b/tests/test_init.py
@@ -3,12 +3,15 @@
 from ast import literal_eval
 import asyncio
 from datetime import datetime as dt
+import ntpath
+import os
 import pathlib
 from unittest.mock import mock_open, patch
 
 import pytest
 from pytest_homeassistant.common import mock_restore_cache
 
+import custom_components.pyscript as pyscript_component
 from custom_components.pyscript import restore_state, trigger
 from custom_components.pyscript.const import DOMAIN
 from custom_components.pyscript.event import Event
@@ -25,7 +28,7 @@
 async def setup_script(hass, notify_q, now, source, script_name="/hello.py"):
     """Initialize and load the given pyscript."""
 
-    scripts = [script_name]
+    scripts = [f"{hass.config.path('pyscript')}{script_name}"]
 
     Function.hass = None
 
@@ -71,6 +74,56 @@ async def wait_until_done(notify_q):
     return await asyncio.wait_for(notify_q.get(), timeout=4)
 
 
+def test_relative_script_path_normalizes_windows_paths():
+    """Script paths should derive portable context names on Windows."""
+    assert (
+        pyscript_component._relative_script_path(  # pylint: disable=protected-access
+            r"C:\config\pyscript\apps\foo\__init__.py", r"C:\config\pyscript", ntpath
+        )
+        == "apps/foo/__init__.py"
+    )
+
+
+def test_requirements_file_matches_windows_and_posix_paths():
+    """Requirements events use path components, not a hard-coded separator."""
+    # pylint: disable=protected-access
+    assert pyscript_component._is_requirements_file(r"C:\config\pyscript\requirements.txt", ntpath)
+    assert pyscript_component._is_requirements_file("/config/pyscript/requirements.txt")
+    assert not pyscript_component._is_requirements_file(r"C:\config\notrequirements.txt", ntpath)
+
+
+@pytest.mark.asyncio
+async def test_windows_paths_create_portable_context_names(pyscript, monkeypatch, caplog):
+    """Exercise the loader with Windows-style relative names without patching os.path."""
+    original = pyscript_component._relative_script_path  # pylint: disable=protected-access
+
+    def windows_relative(path, root):
+        if path.endswith("cross_drive.py"):
+            raise ValueError("paths on different drives")
+        relative = os.path.relpath(path, root).replace(os.sep, "\\")
+        return original(ntpath.join(r"C:\config\pyscript", relative), r"C:\config\pyscript", ntpath)
+
+    monkeypatch.setattr(pyscript_component, "_relative_script_path", windows_relative)
+    pyscript.yaml_config = {DOMAIN: {"apps": {"foo": {}}}}
+    pyscript.config = pyscript.yaml_config
+    pyscript.add_files(
+        {
+            "hello.py": "x = 1",
+            "apps/foo/__init__.py": "x = 1",
+            "scripts/nested/task.py": "x = 1",
+            "scripts/#disabled/skip.py": "x = 1",
+            "scripts/cross_drive.py": "x = 1",
+        }
+    )
+    await pyscript.start()
+
+    names = {name for name, _ in GlobalContextMgr.items()}
+    assert {"file.hello", "apps.foo", "scripts.nested.task"} <= names
+    assert not any("#disabled" in name for name in names)
+    assert "scripts.cross_drive" not in names
+    assert "paths on different drives" in caplog.text
+
+
 @pytest.mark.asyncio
 async def test_setup_makedirs_on_no_dir(hass, caplog):
     """Test setup calls os.makedirs when no dir found."""
@@ -149,7 +202,7 @@ def func1()
 """,
     )
     assert "SyntaxError: expected ':'" in caplog.text
-    assert 'File "/hello.py", line 3' in caplog.text
+    assert f'File "{hass.config.path("pyscript")}/hello.py", line 3' in caplog.text
 
 
 @pytest.mark.asyncio
@@ -165,7 +218,7 @@ async def test_syntax_error2(hass, caplog):
 """,
     )
     assert "SyntaxError: invalid syntax" in caplog.text
-    assert 'File "/hello.py", line 2' in caplog.text
+    assert f'File "{hass.config.path("pyscript")}/hello.py", line 2' in caplog.text
 
 
 @pytest.mark.asyncio
@@ -479,7 +532,7 @@ def func5(var_name=None, value=None):
         # now reload the other source file
         #
         scripts = [
-            "/hello.py",
+            f"{hass.config.path('pyscript')}/hello.py",
         ]
 
         with (