diff --git a/.github/workflows/test_e2e.yaml b/.github/workflows/test_e2e.yaml
index c5bad0f0a1..29c54b18ff 100644
--- a/.github/workflows/test_e2e.yaml
+++ b/.github/workflows/test_e2e.yaml
@@ -16,7 +16,10 @@ concurrency:
 
 jobs:
   tests:
-    runs-on: ubuntu-latest
+    runs-on: ${{ matrix.os }}
+    strategy:
+      matrix:
+        os: [ ubuntu-latest, windows-latest ]
     steps:
       - uses: actions/checkout@v4
         with:
diff --git a/pyproject.toml b/pyproject.toml
index 00af57691e..23e90ccc8c 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -25,7 +25,8 @@ dependencies = [
   "typer==0.9.0",
   "urllib3>=1.21.1,<2.3",
   "GitPython==3.1.42",
-  "pydantic==2.6.3"
+  "pydantic==2.6.3",
+  "oschmod"
 ]
 classifiers = [
   "Development Status :: 3 - Alpha",
diff --git a/requirements.txt b/requirements.txt
new file mode 100644
index 0000000000..c3b41c4498
--- /dev/null
+++ b/requirements.txt
@@ -0,0 +1,17 @@
+coverage==7.4.3
+jinja2==3.1.3
+pluggy==1.4.0
+PyYAML==6.0.1
+rich==13.7.1
+requests==2.31.0
+requirements-parser==0.5.0
+setuptools==69.1.1
+snowflake-connector-python[secure-local-storage]==3.7.1
+strictyaml==1.7.3
+tomlkit==0.12.3
+typer==0.9.0
+urllib3>=1.21.1,<2.3
+GitPython==3.1.42
+pydantic==2.6.3
+oschmod
+pywin32
diff --git a/src/snowflake/cli/api/config.py b/src/snowflake/cli/api/config.py
index 5d844f3173..e11a516acc 100644
--- a/src/snowflake/cli/api/config.py
+++ b/src/snowflake/cli/api/config.py
@@ -15,7 +15,6 @@
 )
 from snowflake.cli.api.secure_path import SecurePath
 from snowflake.cli.api.secure_utils import file_permissions_are_strict
-from snowflake.connector.compat import IS_WINDOWS
 from snowflake.connector.config_manager import CONFIG_MANAGER
 from snowflake.connector.constants import CONFIG_FILE, CONNECTIONS_FILE
 from snowflake.connector.errors import MissingConfigOptionError
@@ -224,13 +223,13 @@ def _get_envs_for_path(*path) -> dict:
 
 
 def _dump_config(conf_file_cache: Dict):
-    with SecurePath(CONFIG_MANAGER.file_path).open("w+") as fh:
+    secure_config_path = SecurePath(CONFIG_MANAGER.file_path)
+    with secure_config_path.open("w+") as fh:
         dump(conf_file_cache, fh)
+    secure_config_path.chmod(0o600)
 
 
 def _check_default_config_files_permissions() -> None:
-    if IS_WINDOWS:
-        return
     if CONNECTIONS_FILE.exists() and not file_permissions_are_strict(CONNECTIONS_FILE):
         raise ConfigFileTooWidePermissionsError(CONNECTIONS_FILE)
     if CONFIG_FILE.exists() and not file_permissions_are_strict(CONFIG_FILE):
diff --git a/src/snowflake/cli/api/exceptions.py b/src/snowflake/cli/api/exceptions.py
index 4ff4acf346..2ebdb3aeb5 100644
--- a/src/snowflake/cli/api/exceptions.py
+++ b/src/snowflake/cli/api/exceptions.py
@@ -5,6 +5,7 @@
 
 from click.exceptions import ClickException
 from snowflake.cli.api.constants import ObjectType
+from snowflake.connector.compat import IS_WINDOWS
 
 
 class EnvironmentVariableNotFoundError(ClickException):
@@ -111,8 +112,14 @@ def __init__(self, path: Path):
 
 class ConfigFileTooWidePermissionsError(ClickException):
     def __init__(self, path: Path):
+        change_permission_message = (
+            "set read and write access only to the current user."
+            if IS_WINDOWS
+            else f'run `chmod 0600 "{path}"`.'
+        )
+
         super().__init__(
-            f'Configuration file {path} has too wide permissions, run `chmod 0600 "{path}"`'
+            f"Configuration file {path} has too wide permissions, {change_permission_message}"
         )
 
 
diff --git a/src/snowflake/cli/api/secure_path.py b/src/snowflake/cli/api/secure_path.py
index d9b6cb211f..d64fdbc6f6 100644
--- a/src/snowflake/cli/api/secure_path.py
+++ b/src/snowflake/cli/api/secure_path.py
@@ -7,6 +7,7 @@
 from pathlib import Path
 from typing import Optional, Union
 
+import oschmod
 from snowflake.cli.api.exceptions import DirectoryIsNotEmptyError, FileTooLargeError
 
 log = logging.getLogger(__name__)
@@ -69,7 +70,7 @@ def chmod(self, permissions_mask: int) -> None:
         log.info(
             "Update permissions of file %s to %s", self._path, oct(permissions_mask)
         )
-        self._path.chmod(permissions_mask)
+        oschmod.set_mode(str(self._path), permissions_mask)
 
     def touch(self, permissions_mask: int = 0o600, exist_ok: bool = True) -> None:
         """
diff --git a/src/snowflake/cli/api/secure_utils.py b/src/snowflake/cli/api/secure_utils.py
index 97f4cd5552..5391278a75 100644
--- a/src/snowflake/cli/api/secure_utils.py
+++ b/src/snowflake/cli/api/secure_utils.py
@@ -1,6 +1,8 @@
 import stat
 from pathlib import Path
 
+import oschmod
+
 
 def file_permissions_are_strict(file_path: Path) -> bool:
     accessible_by_others = (
@@ -12,4 +14,4 @@ def file_permissions_are_strict(file_path: Path) -> bool:
         | stat.S_IXGRP  # executable by group
         | stat.S_IXOTH  # executable by others
     )
-    return (file_path.stat().st_mode & accessible_by_others) == 0
+    return (oschmod.get_mode(str(file_path)) & accessible_by_others) == 0
diff --git a/tests_e2e/__snapshots__/test_config.ambr b/tests_e2e/__snapshots__/test_config.ambr
new file mode 100644
index 0000000000..d977c47bef
--- /dev/null
+++ b/tests_e2e/__snapshots__/test_config.ambr
@@ -0,0 +1,15 @@
+# serializer version: 1
+# name: test_config_file_creation
+  '''
+  No data
+  
+  
+  '''
+# ---
+# name: test_config_file_creation.1
+  '''
+  No data
+  
+  
+  '''
+# ---
diff --git a/tests_e2e/conftest.py b/tests_e2e/conftest.py
index fa28c6dc17..246fa8742e 100644
--- a/tests_e2e/conftest.py
+++ b/tests_e2e/conftest.py
@@ -1,4 +1,5 @@
 import os
+import platform
 import subprocess
 import tempfile
 from pathlib import Path
@@ -10,6 +11,18 @@
 TEST_DIR = Path(__file__).parent
 
 
+@pytest.fixture
+def snowflake_home(monkeypatch):
+    """
+    Set up the default location of config files to [temp_dir]/.snowflake
+    """
+    with tempfile.TemporaryDirectory() as tmp_dir:
+        snowflake_home = Path(tmp_dir) / ".snowflake"
+        snowflake_home.mkdir()
+        monkeypatch.setenv("SNOWFLAKE_HOME", str(snowflake_home))
+        yield snowflake_home
+
+
 @pytest.fixture(scope="session")
 def test_root_path():
     return TEST_DIR
@@ -41,7 +54,7 @@ def snowcli(test_root_path):
         _create_venv(tmp_dir_path)
         _build_snowcli(tmp_dir_path, test_root_path)
         _install_snowcli_with_external_plugin(tmp_dir_path, test_root_path)
-        yield tmp_dir_path / "bin" / "snow"
+        yield _snow_path(tmp_dir_path)
 
 
 @pytest.fixture(autouse=True)
@@ -58,7 +71,7 @@ def _build_snowcli(venv_path: Path, test_root_path: Path) -> None:
         [_python_path(venv_path), "-m", "pip", "install", "--upgrade", "build"]
     )
     subprocess.check_call(
-        [_python_path(venv_path), "-m", "build", test_root_path / ".."]
+        [_python_path(venv_path), "-m", "build", test_root_path.parent]
     )
 
 
@@ -73,7 +86,9 @@ def _install_snowcli_with_external_plugin(
     python = _python_path(venv_path)
     _pip_install(
         python,
-        test_root_path / f"../dist/snowflake_cli_labs-{version}-py3-none-any.whl",
+        test_root_path.parent
+        / "dist"
+        / f"snowflake_cli_labs-{version}-py3-none-any.whl",
     )
     _pip_install(
         python,
@@ -87,4 +102,15 @@ def _install_snowcli_with_external_plugin(
 
 
 def _python_path(venv_path: Path) -> Path:
-    return venv_path / "bin" / "python"
+    return _bin_in_venv_path(venv_path, "python")
+
+
+def _snow_path(venv_path: Path) -> Path:
+    return _bin_in_venv_path(venv_path, "snow")
+
+
+def _bin_in_venv_path(venv_path: Path, bin_name: str) -> Path:
+    if platform.system() == "Windows":
+        return venv_path / "Scripts" / bin_name
+    else:
+        return venv_path / "bin" / bin_name
diff --git a/tests_e2e/test_config.py b/tests_e2e/test_config.py
new file mode 100644
index 0000000000..412d1fbaf0
--- /dev/null
+++ b/tests_e2e/test_config.py
@@ -0,0 +1,12 @@
+import subprocess
+
+import pytest
+
+
+@pytest.mark.e2e
+def test_config_file_creation(snowcli, test_root_path, snowflake_home, snapshot):
+    output1 = subprocess.check_output([snowcli, "connection", "list"], encoding="utf-8")
+    snapshot.assert_match(output1)
+
+    output2 = subprocess.check_output([snowcli, "connection", "list"], encoding="utf-8")
+    snapshot.assert_match(output2)
diff --git a/tests_e2e/test_error_handling.py b/tests_e2e/test_error_handling.py
index db943a7fc9..413822f629 100644
--- a/tests_e2e/test_error_handling.py
+++ b/tests_e2e/test_error_handling.py
@@ -1,10 +1,12 @@
 import os
+import platform
 import subprocess
 
 import pytest
 
 
 @pytest.mark.e2e
+@pytest.mark.skipif(platform.system() == "Windows", reason="Chmod issues on Windows")
 def test_error_traceback_disabled_without_debug(snowcli, test_root_path):
     traceback_msg = "Traceback (most recent call last)"
     config_path = test_root_path / "config" / "malformatted_config.toml"
diff --git a/tests_e2e/test_installation.py b/tests_e2e/test_installation.py
index 0741e751f7..2ad61c48cb 100644
--- a/tests_e2e/test_installation.py
+++ b/tests_e2e/test_installation.py
@@ -1,3 +1,4 @@
+import platform
 import subprocess
 from pathlib import Path
 
@@ -5,6 +6,9 @@
 
 
 @pytest.mark.e2e
+@pytest.mark.skipif(
+    platform.system() == "Windows", reason="Snapshot comparison issues on Windows"
+)
 def test_snow_help(snowcli, snapshot):
     output = subprocess.check_output([snowcli, "--help"], encoding="utf-8")
     snapshot.assert_match(output)