diff --git a/tests_integration/nativeapp/test_post_deploy.py b/tests_integration/nativeapp/test_post_deploy.py
index 549568a0ef..ee9fe6f817 100644
--- a/tests_integration/nativeapp/test_post_deploy.py
+++ b/tests_integration/nativeapp/test_post_deploy.py
@@ -1,7 +1,10 @@
 # Tests that application post-deploy scripts are executed by creating a post_deploy_log table and having each post-deploy script add a record to it
 
+from pathlib import Path
 import pytest
+import yaml
 
+from tests_common import IS_WINDOWS
 from tests_integration.test_utils import (
     row_from_snowflake_session,
 )
@@ -108,16 +111,14 @@ def test_nativeapp_post_deploy(
                 create_version(runner, version, project_args)
             run(runner, base_command, project_args + version_run_args)
 
-            # TODO Remove condition once ApplicationEntity deploy is implemented
-            if base_command == "app":
-                verify_app_post_deploy_log(
-                    snowflake_session,
-                    app_name,
-                    [
-                        {"TEXT": "app-post-deploy-part-1"},
-                        {"TEXT": "app-post-deploy-part-2"},
-                    ],
-                )
+            verify_app_post_deploy_log(
+                snowflake_session,
+                app_name,
+                [
+                    {"TEXT": "app-post-deploy-part-1"},
+                    {"TEXT": "app-post-deploy-part-2"},
+                ],
+            )
 
             verify_pkg_post_deploy_log(
                 snowflake_session,
@@ -133,18 +134,16 @@ def test_nativeapp_post_deploy(
                 create_version(runner, version, project_args)
             run(runner, base_command, project_args + version_run_args)
 
-            # TODO Remove condition once ApplicationEntity deploy is implemented
-            if base_command == "app":
-                verify_app_post_deploy_log(
-                    snowflake_session,
-                    app_name,
-                    [
-                        {"TEXT": "app-post-deploy-part-1"},
-                        {"TEXT": "app-post-deploy-part-2"},
-                        {"TEXT": "app-post-deploy-part-1"},
-                        {"TEXT": "app-post-deploy-part-2"},
-                    ],
-                )
+            verify_app_post_deploy_log(
+                snowflake_session,
+                app_name,
+                [
+                    {"TEXT": "app-post-deploy-part-1"},
+                    {"TEXT": "app-post-deploy-part-2"},
+                    {"TEXT": "app-post-deploy-part-1"},
+                    {"TEXT": "app-post-deploy-part-2"},
+                ],
+            )
             verify_pkg_post_deploy_log(
                 snowflake_session,
                 pkg_name,
@@ -158,18 +157,16 @@ def test_nativeapp_post_deploy(
 
             deploy(runner, base_command, project_args)
 
-            # TODO Remove condition once ApplicationEntity deploy is implemented
-            if base_command == "app":
-                verify_app_post_deploy_log(
-                    snowflake_session,
-                    app_name,
-                    [
-                        {"TEXT": "app-post-deploy-part-1"},
-                        {"TEXT": "app-post-deploy-part-2"},
-                        {"TEXT": "app-post-deploy-part-1"},
-                        {"TEXT": "app-post-deploy-part-2"},
-                    ],
-                )
+            verify_app_post_deploy_log(
+                snowflake_session,
+                app_name,
+                [
+                    {"TEXT": "app-post-deploy-part-1"},
+                    {"TEXT": "app-post-deploy-part-2"},
+                    {"TEXT": "app-post-deploy-part-1"},
+                    {"TEXT": "app-post-deploy-part-2"},
+                ],
+            )
             verify_pkg_post_deploy_log(
                 snowflake_session,
                 pkg_name,
@@ -188,3 +185,88 @@ def test_nativeapp_post_deploy(
                 # need to drop the version before we can teardown
                 drop_version(runner, version, project_args)
             teardown(runner, project_args)
+
+
+@pytest.mark.integration
+@pytest.mark.skipif(
+    not IS_WINDOWS, reason="Testing windows path should only be done on Windows"
+)
+@pytest.mark.parametrize(
+    "base_command,test_project",
+    [
+        ["app", "napp_application_post_deploy_v1"],
+        ["app", "napp_application_post_deploy_v2"],
+        ["ws", "napp_application_post_deploy_v2"],
+    ],
+)
+def test_nativeapp_post_deploy_with_windows_path(
+    runner,
+    snowflake_session,
+    default_username,
+    resource_suffix,
+    nativeapp_project_directory,
+    base_command,
+    test_project,
+):
+    project_name = "myapp"
+    app_name = f"{project_name}_{default_username}{resource_suffix}"
+    pkg_name = f"{project_name}_pkg_{default_username}{resource_suffix}"
+
+    with nativeapp_project_directory(test_project) as tmp_dir:
+        try:
+            snowflake_yml_path = tmp_dir / "snowflake.yml"
+            with open(snowflake_yml_path, "r", encoding="utf-8") as file:
+                yml = yaml.safe_load(file)
+                if yml["definition_version"] >= 2:
+                    artifact = yml["entities"]["pkg"]["artifacts"][0]
+                    pkg_scripts = yml["entities"]["pkg"]["meta"]["post_deploy"]
+                    app_scripts = yml["entities"]["app"]["meta"]["post_deploy"]
+                else:
+                    artifact = yml["native_app"]["artifacts"][0]
+                    pkg_scripts = yml["native_app"]["package"]["post_deploy"]
+                    app_scripts = yml["native_app"]["application"]["post_deploy"]
+
+                # use backslashes in artifacts src
+                artifact["src"] = artifact["src"].replace("/", "\\")
+
+                # use backslashes in post_deploy paths, as well as full paths with backslashes
+                pkg_scripts[0]["sql_script"] = pkg_scripts[0]["sql_script"].replace(
+                    "/", "\\"
+                )
+                pkg_scripts[1]["sql_script"] = str(
+                    (tmp_dir / pkg_scripts[1]["sql_script"]).absolute()
+                )
+
+                # use backslashes in post_deploy paths, as well as full paths with backslashes
+                app_scripts[0]["sql_script"] = app_scripts[0]["sql_script"].replace(
+                    "/", "\\"
+                )
+                app_scripts[1]["sql_script"] = str(
+                    (tmp_dir / app_scripts[1]["sql_script"]).absolute()
+                )
+
+            with open(snowflake_yml_path, "w", encoding="utf-8") as file:
+                yaml.dump(yml, file)
+
+            run(runner, base_command, [])
+
+            verify_app_post_deploy_log(
+                snowflake_session,
+                app_name,
+                [
+                    {"TEXT": "app-post-deploy-part-1"},
+                    {"TEXT": "app-post-deploy-part-2"},
+                ],
+            )
+
+            verify_pkg_post_deploy_log(
+                snowflake_session,
+                pkg_name,
+                [
+                    {"TEXT": "package-post-deploy-part-1"},
+                    {"TEXT": "package-post-deploy-part-2"},
+                ],
+            )
+
+        finally:
+            teardown(runner, [])