diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_messages_system_role_normalization.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_messages_system_role_normalization.py
new file mode 100644
index 00000000000..ee625f15bd1
--- /dev/null
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_messages_system_role_normalization.py
@@ -0,0 +1,201 @@
+"""Unit tests for system role message normalization in AnthropicMessagesConfig.
+
+Covers the should_normalize_system_role_messages() hook, _as_system_content_blocks(),
+and _normalize_system_role_messages() methods.
+"""
+
+from litellm.llms.anthropic.experimental_pass_through.messages.transformation import (
+    AnthropicMessagesConfig,
+)
+
+
+class TestAsSystemContentBlocks:
+    """Test the _as_system_content_blocks helper."""
+
+    def test_none_returns_empty_list(self):
+        result = AnthropicMessagesConfig._as_system_content_blocks(None)
+        assert result == []
+
+    def test_string_returns_text_block(self):
+        result = AnthropicMessagesConfig._as_system_content_blocks("hello")
+        assert result == [{"type": "text", "text": "hello"}]
+
+    def test_list_returns_copy(self):
+        original = [{"type": "text", "text": "block1"}, {"type": "text", "text": "block2"}]
+        result = AnthropicMessagesConfig._as_system_content_blocks(original)
+        assert result == original
+        assert result is not original
+
+    def test_dict_wraps_in_list(self):
+        block = {"type": "text", "text": "wrapped"}
+        result = AnthropicMessagesConfig._as_system_content_blocks(block)
+        assert result == [block]
+
+
+class TestNormalizeSystemRoleMessages:
+    """Test the _normalize_system_role_messages method."""
+
+    def _make_config(self):
+        return AnthropicMessagesConfig()
+
+    def test_no_system_role_messages_is_noop(self):
+        config = self._make_config()
+        messages = [{"role": "user", "content": "hello"}]
+        params = {}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == messages
+        assert result_params == {}
+
+    def test_single_system_message_moved_to_top_level(self):
+        config = self._make_config()
+        messages = [
+            {"role": "system", "content": "You are helpful"},
+            {"role": "user", "content": "hello"},
+        ]
+        params = {}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == [{"role": "user", "content": "hello"}]
+        assert result_params["system"] == [
+            {"type": "text", "text": "You are helpful"}
+        ]
+
+    def test_existing_system_merged_with_system_messages(self):
+        config = self._make_config()
+        messages = [
+            {"role": "system", "content": "Extra instruction"},
+            {"role": "user", "content": "hello"},
+        ]
+        params = {"system": "Base instruction"}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == [{"role": "user", "content": "hello"}]
+        assert result_params["system"] == [
+            {"type": "text", "text": "Base instruction"},
+            {"type": "text", "text": "Extra instruction"},
+        ]
+
+    def test_multiple_system_messages_all_moved(self):
+        config = self._make_config()
+        messages = [
+            {"role": "system", "content": "First"},
+            {"role": "user", "content": "hi"},
+            {"role": "system", "content": "Second"},
+        ]
+        params = {}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == [{"role": "user", "content": "hi"}]
+        assert result_params["system"] == [
+            {"type": "text", "text": "First"},
+            {"type": "text", "text": "Second"},
+        ]
+
+    def test_system_with_list_content_preserved(self):
+        config = self._make_config()
+        messages = [
+            {
+                "role": "system",
+                "content": [{"type": "text", "text": "Block content"}],
+            },
+            {"role": "user", "content": "hello"},
+        ]
+        params = {}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == [{"role": "user", "content": "hello"}]
+        assert result_params["system"] == [
+            {"type": "text", "text": "Block content"}
+        ]
+
+    def test_existing_system_as_list_merged_correctly(self):
+        config = self._make_config()
+        messages = [
+            {"role": "system", "content": "Extra"},
+            {"role": "user", "content": "hello"},
+        ]
+        params = {"system": [{"type": "text", "text": "Existing block"}]}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == [{"role": "user", "content": "hello"}]
+        assert result_params["system"] == [
+            {"type": "text", "text": "Existing block"},
+            {"type": "text", "text": "Extra"},
+        ]
+
+    def test_empty_system_content_removes_system_param(self):
+        config = self._make_config()
+        messages = [
+            {"role": "system", "content": None},
+            {"role": "user", "content": "hello"},
+        ]
+        params = {}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == [{"role": "user", "content": "hello"}]
+        assert "system" not in result_params
+
+    def test_non_dict_messages_preserved(self):
+        config = self._make_config()
+        messages = [
+            {"role": "system", "content": "sys"},
+            "not a dict",
+            {"role": "user", "content": "hello"},
+        ]
+        params = {}
+
+        result_messages, result_params = config._normalize_system_role_messages(
+            messages, params
+        )
+
+        assert result_messages == [
+            "not a dict",
+            {"role": "user", "content": "hello"},
+        ]
+        assert result_params["system"] == [{"type": "text", "text": "sys"}]
+
+
+class TestShouldNormalizeSystemRoleMessages:
+    """Test the opt-in flag defaults and overrides."""
+
+    def test_base_class_defaults_to_false(self):
+        config = AnthropicMessagesConfig()
+        assert config.should_normalize_system_role_messages() is False
+
+    def test_vertex_ai_overrides_to_true(self):
+        from litellm.llms.vertex_ai.vertex_ai_partner_models.anthropic.experimental_pass_through.transformation import (
+            VertexAIPartnerModelsAnthropicMessagesConfig,
+        )
+
+        config = VertexAIPartnerModelsAnthropicMessagesConfig()
+        assert config.should_normalize_system_role_messages() is True
+
+    def test_azure_ai_overrides_to_true(self):
+        from litellm.llms.azure_ai.anthropic.messages_transformation import (
+            AzureAnthropicMessagesConfig,
+        )
+
+        config = AzureAnthropicMessagesConfig()
+        assert config.should_normalize_system_role_messages() is True