test(tooling): add whitespace and empty list validation tests

Add tests for whitespace-only string validation in ChatHistoryMessage and
ChatMessageRequest (CRM-012). Add test for empty chat_history list
validation in send_chat_history (CRM-011). Update HTTP error test to
match new aiohttp.ClientResponseError format.

Co-Authored-By: Claude Opus 4.5 <[email protected]>

Author: Johan Broberg

tests/tooling/models/test_chat_history_message.py

@@ -94,3 +94,48 @@ def test_chat_history_message_preserves_timestamp_precision(self):
         # Assert
         assert message.timestamp == timestamp
         assert "2024-01-15T10:30:45.123000" in message_dict["timestamp"]
+
+    def test_chat_history_message_rejects_whitespace_only_id(self):
+        """Test that ChatHistoryMessage rejects whitespace-only id."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="id cannot be empty"):
+            ChatHistoryMessage("   ", "user", "Content", timestamp)
+
+    def test_chat_history_message_rejects_whitespace_only_role(self):
+        """Test that ChatHistoryMessage rejects whitespace-only role."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="role cannot be empty"):
+            ChatHistoryMessage("msg-1", "   ", "Content", timestamp)
+
+    def test_chat_history_message_rejects_whitespace_only_content(self):
+        """Test that ChatHistoryMessage rejects whitespace-only content."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="content cannot be empty"):
+            ChatHistoryMessage("msg-1", "user", "   ", timestamp)
+
+    def test_chat_history_message_rejects_tab_only_id(self):
+        """Test that ChatHistoryMessage rejects tab-only id."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="id cannot be empty"):
+            ChatHistoryMessage("\t", "user", "Content", timestamp)
+
+    def test_chat_history_message_rejects_newline_only_content(self):
+        """Test that ChatHistoryMessage rejects newline-only content."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="content cannot be empty"):
+            ChatHistoryMessage("msg-1", "user", "\n\n", timestamp)

tests/tooling/models/test_chat_message_request.py

@@ -103,3 +103,49 @@ def test_chat_message_request_with_multiple_messages(self):
         assert result["chatHistory"][0]["id"] == "msg-1"
         assert result["chatHistory"][1]["id"] == "msg-2"
         assert result["chatHistory"][2]["id"] == "msg-3"
+
+    def test_chat_message_request_rejects_whitespace_only_conversation_id(self):
+        """Test that ChatMessageRequest rejects whitespace-only conversation_id."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+        message = ChatHistoryMessage("msg-1", "user", "Hello", timestamp)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="conversation_id cannot be empty"):
+            ChatMessageRequest("   ", "msg-456", "How are you?", [message])
+
+    def test_chat_message_request_rejects_whitespace_only_message_id(self):
+        """Test that ChatMessageRequest rejects whitespace-only message_id."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+        message = ChatHistoryMessage("msg-1", "user", "Hello", timestamp)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="message_id cannot be empty"):
+            ChatMessageRequest("conv-123", "   ", "How are you?", [message])
+
+    def test_chat_message_request_rejects_whitespace_only_user_message(self):
+        """Test that ChatMessageRequest rejects whitespace-only user_message."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+        message = ChatHistoryMessage("msg-1", "user", "Hello", timestamp)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="user_message cannot be empty"):
+            ChatMessageRequest("conv-123", "msg-456", "   ", [message])
+
+    def test_chat_message_request_rejects_tab_only_conversation_id(self):
+        """Test that ChatMessageRequest rejects tab-only conversation_id."""
+        # Arrange
+        timestamp = datetime.now(timezone.utc)
+        message = ChatHistoryMessage("msg-1", "user", "Hello", timestamp)
+
+        # Act & Assert
+        with pytest.raises(ValueError, match="conversation_id cannot be empty"):
+            ChatMessageRequest("\t\t", "msg-456", "How are you?", [message])
+
+    def test_chat_message_request_rejects_none_chat_history(self):
+        """Test that ChatMessageRequest rejects None chat_history."""
+        # Act & Assert
+        with pytest.raises(ValueError, match="chat_history cannot be empty"):
+            ChatMessageRequest("conv-123", "msg-456", "How are you?", None)

tests/tooling/services/test_send_chat_history.py

@@ -92,7 +92,9 @@ async def test_send_chat_history_http_error(
             # Assert
             assert result.succeeded is False
             assert len(result.errors) == 1
-            assert "HTTP 500" in str(result.errors[0].message)
+            # Error now uses aiohttp.ClientResponseError which formats as "status, message=..."
+            assert "500" in str(result.errors[0].message)
+            assert "Internal Server Error" in str(result.errors[0].message)
 
     @pytest.mark.asyncio
     async def test_send_chat_history_with_options(
@@ -128,7 +130,7 @@ async def test_send_chat_history_with_options(
     async def test_send_chat_history_validates_turn_context(self, service, chat_history_messages):
         """Test that send_chat_history validates turn_context parameter."""
         # Act & Assert
-        with pytest.raises(ValueError, match="turn_context cannot be empty or None"):
+        with pytest.raises(ValueError, match="turn_context cannot be None"):
             await service.send_chat_history(None, chat_history_messages)
 
     @pytest.mark.asyncio
@@ -137,9 +139,18 @@ async def test_send_chat_history_validates_chat_history_messages(
     ):
         """Test that send_chat_history validates chat_history_messages parameter."""
         # Act & Assert
-        with pytest.raises(ValueError, match="chat_history_messages cannot be empty or None"):
+        with pytest.raises(ValueError, match="chat_history_messages cannot be None or empty"):
             await service.send_chat_history(mock_turn_context, None)
 
+    @pytest.mark.asyncio
+    async def test_send_chat_history_validates_empty_chat_history_list(
+        self, service, mock_turn_context
+    ):
+        """Test that send_chat_history validates empty chat_history list."""
+        # Act & Assert
+        with pytest.raises(ValueError, match="chat_history_messages cannot be None or empty"):
+            await service.send_chat_history(mock_turn_context, [])
+
     @pytest.mark.asyncio
     async def test_send_chat_history_validates_activity(self, service, chat_history_messages):
         """Test that send_chat_history validates turn_context.activity."""