diff --git a/tests/test_litellm/proxy/client/cli/test_claude_settings.py b/tests/test_litellm/proxy/client/cli/test_claude_settings.py
index cf52d41e963..cfada5ab447 100644
--- a/tests/test_litellm/proxy/client/cli/test_claude_settings.py
+++ b/tests/test_litellm/proxy/client/cli/test_claude_settings.py
@@ -201,6 +201,7 @@ class TestConflictingOwnersOfTheSettingsFile:
 
 
 class TestDoesNotDestroyUserOwnedStructure:
+    @pytest.mark.skipif(sys.platform == "win32", reason="symlink creation needs elevation or Developer Mode on Windows")
     def test_writes_through_a_symlinked_settings_file(self, tmp_path):
         """os.replace() swaps the symlink for a regular file, detaching a dotfiles repo.
 
@@ -265,6 +266,7 @@ class TestConfigureStatePath:
         default_settings, default_state = default_paths
         assert configure_state_path(default_settings) == default_state
 
+    @pytest.mark.skipif(sys.platform == "win32", reason="symlink creation needs elevation or Developer Mode on Windows")
     def test_a_symlink_alias_of_the_default_file_shares_its_receipt(self, default_paths):
         default_settings, default_state = default_paths
         default_settings.parent.mkdir(parents=True)
@@ -713,6 +715,7 @@ class TestConfigureAndUnconfigure:
         finally:
             rig.state.parent.chmod(0o700)
 
+    @pytest.mark.skipif(sys.platform == "win32", reason="symlink creation needs elevation or Developer Mode on Windows")
     def test_configure_writes_through_a_symlinked_settings_file(self, tmp_path):
         target = tmp_path / "dotfiles" / "settings.json"
         target.parent.mkdir()
diff --git a/tests/test_litellm/proxy/common_utils/test_static_asset_utils.py b/tests/test_litellm/proxy/common_utils/test_static_asset_utils.py
index 593158515a5..31b0dfe9249 100644
--- a/tests/test_litellm/proxy/common_utils/test_static_asset_utils.py
+++ b/tests/test_litellm/proxy/common_utils/test_static_asset_utils.py
@@ -7,6 +7,7 @@ arbitrary local image paths working while refusing non-image files like
 """
 
 import os
+import sys
 
 import pytest
 
@@ -52,6 +53,7 @@ class TestResolveValidatedLocalImagePath:
         result = resolve_validated_local_image_path("/proc/self/environ")
         assert result is None
 
+    @pytest.mark.skipif(sys.platform == "win32", reason="symlink creation needs elevation or Developer Mode on Windows")
     def test_rejects_symlink_pointing_to_non_image(self, tmp_path):
         secret = tmp_path / "secret.txt"
         secret.write_text("password=hunter2")
@@ -62,6 +64,7 @@ class TestResolveValidatedLocalImagePath:
 
         assert result is None
 
+    @pytest.mark.skipif(sys.platform == "win32", reason="symlink creation needs elevation or Developer Mode on Windows")
     def test_accepts_symlink_pointing_to_image(self, tmp_path):
         logo = tmp_path / "real_logo.png"
         logo.write_bytes(b"\x89PNG\r\n\x1a\nfake png body")