test: Add comprehensive edge case tests for ChatModel, ListOutputConverter, and ToolExecutionResult

spring-ai-model/src/test/java/org/springframework/ai/chat/ChatModelTests.java

@@ -26,6 +26,7 @@
 import org.springframework.ai.chat.prompt.Prompt;
 
 import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.AssertionsForClassTypes.assertThatThrownBy;
 import static org.mockito.ArgumentMatchers.any;
 import static org.mockito.ArgumentMatchers.anyString;
 import static org.mockito.ArgumentMatchers.eq;
@@ -139,4 +140,139 @@ void generateWithWhitespaceOnlyStringHandlesCorrectly() {
 		verify(mockClient, times(1)).call(eq(userMessage));
 	}
 
+	@Test
+	void generateWhenPromptCallThrowsExceptionPropagatesCorrectly() {
+		String userMessage = "Test message";
+		RuntimeException expectedException = new RuntimeException("API call failed");
+
+		ChatModel mockClient = Mockito.mock(ChatModel.class);
+
+		doCallRealMethod().when(mockClient).call(anyString());
+		given(mockClient.call(any(Prompt.class))).willThrow(expectedException);
+
+		assertThatThrownBy(() -> mockClient.call(userMessage)).isEqualTo(expectedException);
+
+		verify(mockClient, times(1)).call(eq(userMessage));
+		verify(mockClient, times(1)).call(isA(Prompt.class));
+	}
+
+	@Test
+	void generateWhenResponseIsNullHandlesGracefully() {
+		String userMessage = "Test message";
+
+		ChatModel mockClient = Mockito.mock(ChatModel.class);
+
+		doCallRealMethod().when(mockClient).call(anyString());
+		given(mockClient.call(any(Prompt.class))).willReturn(null);
+
+		assertThatThrownBy(() -> mockClient.call(userMessage)).isInstanceOf(NullPointerException.class);
+
+		verify(mockClient, times(1)).call(eq(userMessage));
+		verify(mockClient, times(1)).call(isA(Prompt.class));
+	}
+
+	@Test
+	void generateWhenAssistantMessageIsNullHandlesGracefully() {
+		String userMessage = "Test message";
+
+		ChatModel mockClient = Mockito.mock(ChatModel.class);
+
+		Generation generation = Mockito.mock(Generation.class);
+		given(generation.getOutput()).willReturn(null);
+
+		ChatResponse response = Mockito.mock(ChatResponse.class);
+		given(response.getResult()).willReturn(generation);
+
+		doCallRealMethod().when(mockClient).call(anyString());
+		given(mockClient.call(any(Prompt.class))).willReturn(response);
+
+		assertThatThrownBy(() -> mockClient.call(userMessage)).isInstanceOf(NullPointerException.class);
+
+		verify(mockClient, times(1)).call(eq(userMessage));
+		verify(generation, times(1)).getOutput();
+	}
+
+	@Test
+	void generateWhenAssistantMessageTextIsNullReturnsNull() {
+		String userMessage = "Test message";
+
+		ChatModel mockClient = Mockito.mock(ChatModel.class);
+
+		AssistantMessage mockAssistantMessage = Mockito.mock(AssistantMessage.class);
+		given(mockAssistantMessage.getText()).willReturn(null);
+
+		Generation generation = Mockito.mock(Generation.class);
+		given(generation.getOutput()).willReturn(mockAssistantMessage);
+
+		ChatResponse response = Mockito.mock(ChatResponse.class);
+		given(response.getResult()).willReturn(generation);
+
+		doCallRealMethod().when(mockClient).call(anyString());
+		given(mockClient.call(any(Prompt.class))).willReturn(response);
+
+		String result = mockClient.call(userMessage);
+
+		assertThat(result).isNull();
+		verify(mockClient, times(1)).call(eq(userMessage));
+		verify(mockAssistantMessage, times(1)).getText();
+	}
+
+	@Test
+	void generateWithMultilineStringHandlesCorrectly() {
+		String userMessage = "Line 1\nLine 2\r\nLine 3\rLine 4";
+		String responseMessage = "Multiline input processed";
+
+		ChatModel mockClient = Mockito.mock(ChatModel.class);
+
+		AssistantMessage mockAssistantMessage = Mockito.mock(AssistantMessage.class);
+		given(mockAssistantMessage.getText()).willReturn(responseMessage);
+
+		Generation generation = Mockito.mock(Generation.class);
+		given(generation.getOutput()).willReturn(mockAssistantMessage);
+
+		ChatResponse response = Mockito.mock(ChatResponse.class);
+		given(response.getResult()).willReturn(generation);
+
+		doCallRealMethod().when(mockClient).call(anyString());
+		given(mockClient.call(any(Prompt.class))).willReturn(response);
+
+		String result = mockClient.call(userMessage);
+
+		assertThat(result).isEqualTo(responseMessage);
+		verify(mockClient, times(1)).call(eq(userMessage));
+	}
+
+	@Test
+	void generateMultipleTimesWithSameClientMaintainsState() {
+		ChatModel mockClient = Mockito.mock(ChatModel.class);
+
+		doCallRealMethod().when(mockClient).call(anyString());
+
+		// First call
+		setupMockResponse(mockClient, "Response 1");
+		String result1 = mockClient.call("Message 1");
+		assertThat(result1).isEqualTo("Response 1");
+
+		// Second call
+		setupMockResponse(mockClient, "Response 2");
+		String result2 = mockClient.call("Message 2");
+		assertThat(result2).isEqualTo("Response 2");
+
+		verify(mockClient, times(2)).call(anyString());
+		verify(mockClient, times(2)).call(any(Prompt.class));
+	}
+
+	private void setupMockResponse(ChatModel mockClient, String responseText) {
+		AssistantMessage mockAssistantMessage = Mockito.mock(AssistantMessage.class);
+		given(mockAssistantMessage.getText()).willReturn(responseText);
+
+		Generation generation = Mockito.mock(Generation.class);
+		given(generation.getOutput()).willReturn(mockAssistantMessage);
+
+		ChatResponse response = Mockito.mock(ChatResponse.class);
+		given(response.getResult()).willReturn(generation);
+
+		given(mockClient.call(any(Prompt.class))).willReturn(response);
+	}
+
 }

spring-ai-model/src/test/java/org/springframework/ai/converter/ListOutputConverterTest.java

@@ -178,4 +178,43 @@ void csvWithOnlyWhitespace() {
 		assertThat(list.get(0)).isBlank();
 	}
 
+	@Test
+	void csvWithCommasInQuotedValues() {
+		String csvAsString = "\"value, with, commas\", normal, \"another, comma\"";
+		List<String> list = this.listOutputConverter.convert(csvAsString);
+		assertThat(list).isNotEmpty();
+		assertThat(list).doesNotContainNull();
+	}
+
+	@Test
+	void csvWithNewlinesInQuotedValues() {
+		String csvAsString = "\"line1\nline2\", normal, \"another\nline\"";
+		List<String> list = this.listOutputConverter.convert(csvAsString);
+		assertThat(list).isNotEmpty();
+		assertThat(list).doesNotContainNull();
+	}
+
+	@Test
+	void csvWithMixedQuotingStyles() {
+		String csvAsString = "'single quoted', \"double quoted\", `backtick quoted`, unquoted";
+		List<String> list = this.listOutputConverter.convert(csvAsString);
+		assertThat(list).hasSize(4);
+		assertThat(list).doesNotContainNull();
+	}
+
+	@Test
+	void csvWithOnlyCommasAndSpaces() {
+		String csvAsString = " , , , ";
+		List<String> list = this.listOutputConverter.convert(csvAsString);
+		assertThat(list).hasSize(4);
+		assertThat(list).allMatch(String::isEmpty);
+	}
+
+	@Test
+	void csvWithMalformedQuoting() {
+		String csvAsString = "\"unclosed quote, normal, \"properly closed\"";
+		List<String> list = this.listOutputConverter.convert(csvAsString);
+		assertThat(list).isNotEmpty();
+	}
+
 }

spring-ai-model/src/test/java/org/springframework/ai/model/tool/ToolExecutionResultTests.java

@@ -140,4 +140,51 @@ void whenBuilderCalledWithoutConversationHistoryThenThrowsException() {
 		assertThat(toolExecutionResult.conversationHistory()).isEmpty();
 	}
 
+	@Test
+	void whenMultipleToolResponseMessagesOnlyLastOneIsProcessed() {
+		var toolExecutionResult = ToolExecutionResult.builder()
+			.conversationHistory(List.of(new AssistantMessage("First response"),
+					new ToolResponseMessage(
+							List.of(new ToolResponseMessage.ToolResponse("1", "old_tool", "Old response"))),
+					new AssistantMessage("Second response"),
+					new ToolResponseMessage(
+							List.of(new ToolResponseMessage.ToolResponse("2", "new_tool", "New response")))))
+			.build();
+
+		var generations = ToolExecutionResult.buildGenerations(toolExecutionResult);
+
+		assertThat(generations).hasSize(1);
+		assertThat(generations.get(0).getOutput().getText()).isEqualTo("New response");
+		assertThat((String) generations.get(0).getMetadata().get(ToolExecutionResult.METADATA_TOOL_NAME))
+			.isEqualTo("new_tool");
+	}
+
+	@Test
+	void whenToolResponseWithEmptyToolNameThenMetadataContainsEmptyString() {
+		var toolExecutionResult = ToolExecutionResult.builder()
+			.conversationHistory(List.of(new ToolResponseMessage(
+					List.of(new ToolResponseMessage.ToolResponse("1", "", "Response content")))))
+			.build();
+
+		var generations = ToolExecutionResult.buildGenerations(toolExecutionResult);
+
+		assertThat(generations).hasSize(1);
+		assertThat((String) generations.get(0).getMetadata().get(ToolExecutionResult.METADATA_TOOL_NAME)).isEmpty();
+	}
+
+	@Test
+	void whenToolResponseWithNullToolIdThenGenerationStillCreated() {
+		var toolExecutionResult = ToolExecutionResult.builder()
+			.conversationHistory(List.of(new ToolResponseMessage(
+					List.of(new ToolResponseMessage.ToolResponse(null, "tool", "Response content")))))
+			.build();
+
+		var generations = ToolExecutionResult.buildGenerations(toolExecutionResult);
+
+		assertThat(generations).hasSize(1);
+		assertThat(generations.get(0).getOutput().getText()).isEqualTo("Response content");
+		assertThat((String) generations.get(0).getMetadata().get(ToolExecutionResult.METADATA_TOOL_NAME))
+			.isEqualTo("tool");
+	}
+
 }