diff --git a/pyrit/message_normalizer/conversation_context_normalizer.py b/pyrit/message_normalizer/conversation_context_normalizer.py
index 46e3c96308..54f4bf0166 100644
--- a/pyrit/message_normalizer/conversation_context_normalizer.py
+++ b/pyrit/message_normalizer/conversation_context_normalizer.py
@@ -23,6 +23,13 @@ class ConversationContextNormalizer(MessageStringNormalizer):
         ...
     """
 
+    _ROLE_LABELS = {
+        "user": "User",
+        "assistant": "Assistant",
+        "tool": "Tool",
+        "developer": "Developer",
+    }
+
     async def normalize_string_async(self, messages: list[Message]) -> str:
         """
         Normalize a list of messages into a turn-based context string.
@@ -55,7 +62,7 @@ async def normalize_string_async(self, messages: list[Message]) -> str:
 
                 # Format the piece content
                 content = self._format_piece_content(piece)
-                role_label = "User" if piece.api_role == "user" else "Assistant"
+                role_label = self._ROLE_LABELS.get(piece.api_role, piece.api_role.capitalize())
                 context_parts.append(f"{role_label}: {content}")
 
         return "\n".join(context_parts)
diff --git a/tests/unit/message_normalizer/test_conversation_context_normalizer.py b/tests/unit/message_normalizer/test_conversation_context_normalizer.py
index 855668e72d..4054f790cb 100644
--- a/tests/unit/message_normalizer/test_conversation_context_normalizer.py
+++ b/tests/unit/message_normalizer/test_conversation_context_normalizer.py
@@ -108,3 +108,31 @@ async def test_shows_original_if_different_from_converted(self):
 
         assert "converted text" in result
         assert "(original: original text)" in result
+
+    @pytest.mark.asyncio
+    async def test_preserves_tool_role_label(self):
+        """Test that tool messages keep the Tool label in context output."""
+        normalizer = ConversationContextNormalizer()
+        messages = [
+            _make_message("user", "Call the weather tool"),
+            _make_message("tool", "72F and sunny"),
+        ]
+
+        result = await normalizer.normalize_string_async(messages)
+
+        assert "Tool: 72F and sunny" in result
+        assert "Assistant: 72F and sunny" not in result
+
+    @pytest.mark.asyncio
+    async def test_preserves_developer_role_label(self):
+        """Test that developer messages keep the Developer label in context output."""
+        normalizer = ConversationContextNormalizer()
+        messages = [
+            _make_message("user", "Use concise units"),
+            _make_message("developer", "Prefer metric units"),
+        ]
+
+        result = await normalizer.normalize_string_async(messages)
+
+        assert "Developer: Prefer metric units" in result
+        assert "Assistant: Prefer metric units" not in result