diff --git a/python/semantic_kernel/connectors/openapi_plugin/server_url_validator.py b/python/semantic_kernel/connectors/openapi_plugin/server_url_validator.py
index ed8258fce36a..9081d3f2ae2d 100644
--- a/python/semantic_kernel/connectors/openapi_plugin/server_url_validator.py
+++ b/python/semantic_kernel/connectors/openapi_plugin/server_url_validator.py
@@ -117,8 +117,8 @@ def _matches_path_prefix(url_path: str, base_path: str) -> bool:
     url_path = url_path or "/"
     base_path = base_path or "/"
 
-    if url_path.lower() == base_path.lower():
+    if url_path == base_path:
         return True
 
     base_path_with_slash = base_path if base_path.endswith("/") else f"{base_path}/"
-    return url_path.lower().startswith(base_path_with_slash.lower())
+    return url_path.startswith(base_path_with_slash)
diff --git a/python/tests/unit/connectors/openapi_plugin/test_openapi_runner.py b/python/tests/unit/connectors/openapi_plugin/test_openapi_runner.py
index b990ebfb834e..838cf245844c 100644
--- a/python/tests/unit/connectors/openapi_plugin/test_openapi_runner.py
+++ b/python/tests/unit/connectors/openapi_plugin/test_openapi_runner.py
@@ -6,6 +6,10 @@
 import pytest
 
 from semantic_kernel.connectors.openapi_plugin.models.rest_api_operation import RestApiOperation
+from semantic_kernel.connectors.openapi_plugin.models.rest_api_parameter import RestApiParameter
+from semantic_kernel.connectors.openapi_plugin.models.rest_api_parameter_location import (
+    RestApiParameterLocation,
+)
 from semantic_kernel.connectors.openapi_plugin.models.rest_api_payload import RestApiPayload
 from semantic_kernel.connectors.openapi_plugin.openapi_manager import OpenApiRunner
 from semantic_kernel.connectors.openapi_plugin.server_url_validator import ServerUrlValidationOptions
@@ -328,6 +332,61 @@ async def mock_request(*args, **kwargs):
     assert result == "response text"
 
 
+@pytest.mark.parametrize(
+    ("method", "route", "is_allowed"),
+    [
+        ("GET", "safe", True),
+        ("POST", "safe", True),
+        ("GET", "SAFE", False),
+        ("POST", "SAFE", False),
+    ],
+)
+async def test_run_operation_enforces_allowed_base_url_path_case_before_authentication(method, route, is_allowed):
+    runner = OpenApiRunner(
+        {},
+        server_url_validation_options=ServerUrlValidationOptions(
+            allowed_base_urls=["https://api.example.com/api/safe"]
+        ),
+    )
+    operation = RestApiOperation(
+        id="caseSensitiveOperation",
+        method=method,
+        servers=[{"url": "https://api.example.com"}],
+        path="/api/{route}",
+        params=[
+            RestApiParameter(
+                name="route",
+                type="string",
+                location=RestApiParameterLocation.PATH,
+                is_required=True,
+            )
+        ],
+    )
+    response = MagicMock()
+    response.text = "response text"
+    runner.http_client = AsyncMock()
+    runner.http_client.headers = {}
+    runner.http_client.request = AsyncMock(return_value=response)
+    runner.auth_callback = AsyncMock(return_value={"Authorization": "******"})
+
+    if is_allowed:
+        result = await runner.run_operation(operation, {"route": route})
+
+        assert result == "response text"
+        runner.auth_callback.assert_awaited_once_with()
+        runner.http_client.request.assert_awaited_once()
+        request = runner.http_client.request.await_args.kwargs
+        assert request["method"] == method
+        assert request["url"] == "https://api.example.com/api/safe"
+        assert request["headers"]["Authorization"] == "******"
+    else:
+        with pytest.raises(FunctionExecutionException, match="allowed base URLs"):
+            await runner.run_operation(operation, {"route": route})
+
+        runner.auth_callback.assert_not_awaited()
+        runner.http_client.request.assert_not_awaited()
+
+
 async def test_run_operation_blocks_disallowed_url_before_request():
     runner = OpenApiRunner({})
     operation = MagicMock()
diff --git a/python/tests/unit/connectors/openapi_plugin/test_server_url_validator.py b/python/tests/unit/connectors/openapi_plugin/test_server_url_validator.py
index e6d6f900e6ec..67e43493e78f 100644
--- a/python/tests/unit/connectors/openapi_plugin/test_server_url_validator.py
+++ b/python/tests/unit/connectors/openapi_plugin/test_server_url_validator.py
@@ -132,6 +132,21 @@ async def test_validate_server_url_rejects_when_allowed_base_urls_do_not_match()
         await validate_server_url("https://api.example.com/v2/orders", options)
 
 
+@pytest.mark.parametrize("path", ["/api/safe", "/api/safe/orders"])
+async def test_validate_server_url_allows_matching_allowed_base_url_path_case(path):
+    options = ServerUrlValidationOptions(allowed_base_urls=["https://API.EXAMPLE.COM:443/api/safe"])
+
+    await validate_server_url(f"https://api.example.com{path}", options)
+
+
+@pytest.mark.parametrize("path", ["/api/SAFE", "/api/SAFE/orders", "/api/private", "/api/safeX"])
+async def test_validate_server_url_rejects_non_matching_allowed_base_url_path(path):
+    options = ServerUrlValidationOptions(allowed_base_urls=["https://api.example.com/api/safe"])
+
+    with pytest.raises(FunctionExecutionException, match="allowed base URLs"):
+        await validate_server_url(f"https://api.example.com{path}", options)
+
+
 @pytest.mark.parametrize("url", ["https://10.0.0.5/", "https://[fec0::1]/"])
 async def test_validate_server_url_allows_private_network_access_after_scheme_gate(url):
     options = ServerUrlValidationOptions(allow_private_network_access=True)