diff --git a/spring-ai-model/src/test/java/org/springframework/ai/model/tool/DefaultToolCallingManagerTest.java b/spring-ai-model/src/test/java/org/springframework/ai/model/tool/DefaultToolCallingManagerTest.java
index ce775b20cd5..bd60639c323 100644
--- a/spring-ai-model/src/test/java/org/springframework/ai/model/tool/DefaultToolCallingManagerTest.java
+++ b/spring-ai-model/src/test/java/org/springframework/ai/model/tool/DefaultToolCallingManagerTest.java
@@ -155,4 +155,272 @@ public String call(String toolInput) {
 		assertThatNoException().isThrownBy(() -> managerWithCallback.executeToolCalls(prompt, chatResponse));
 	}
 
+	@Test
+	void shouldHandleMultipleToolCallsInSingleResponse() {
+		// Create mock tool callbacks
+		ToolCallback toolCallback1 = new ToolCallback() {
+			@Override
+			public ToolDefinition getToolDefinition() {
+				return DefaultToolDefinition.builder()
+					.name("tool1")
+					.description("First tool")
+					.inputSchema("{\"type\": \"object\", \"properties\": {\"param\": {\"type\": \"string\"}}}")
+					.build();
+			}
+
+			@Override
+			public ToolMetadata getToolMetadata() {
+				return ToolMetadata.builder().build();
+			}
+
+			@Override
+			public String call(String toolInput) {
+				return "{\"result\": \"tool1_success\"}";
+			}
+		};
+
+		ToolCallback toolCallback2 = new ToolCallback() {
+			@Override
+			public ToolDefinition getToolDefinition() {
+				return DefaultToolDefinition.builder()
+					.name("tool2")
+					.description("Second tool")
+					.inputSchema("{\"type\": \"object\", \"properties\": {\"value\": {\"type\": \"number\"}}}")
+					.build();
+			}
+
+			@Override
+			public ToolMetadata getToolMetadata() {
+				return ToolMetadata.builder().build();
+			}
+
+			@Override
+			public String call(String toolInput) {
+				return "{\"result\": \"tool2_success\"}";
+			}
+		};
+
+		// Create multiple ToolCalls
+		AssistantMessage.ToolCall toolCall1 = new AssistantMessage.ToolCall("1", "function", "tool1",
+				"{\"param\": \"test\"}");
+		AssistantMessage.ToolCall toolCall2 = new AssistantMessage.ToolCall("2", "function", "tool2",
+				"{\"value\": 42}");
+
+		// Create ChatResponse with multiple tool calls
+		AssistantMessage assistantMessage = AssistantMessage.builder()
+			.content("")
+			.properties(Map.of())
+			.toolCalls(List.of(toolCall1, toolCall2))
+			.build();
+		Generation generation = new Generation(assistantMessage);
+		ChatResponse chatResponse = new ChatResponse(List.of(generation));
+
+		Prompt prompt = new Prompt(List.of(new UserMessage("test multiple tools")));
+
+		DefaultToolCallingManager manager = DefaultToolCallingManager.builder()
+			.observationRegistry(ObservationRegistry.NOOP)
+			.toolCallbackResolver(toolName -> {
+				if ("tool1".equals(toolName)) {
+					return toolCallback1;
+				}
+				if ("tool2".equals(toolName)) {
+					return toolCallback2;
+				}
+				return null;
+			})
+			.build();
+
+		assertThatNoException().isThrownBy(() -> manager.executeToolCalls(prompt, chatResponse));
+	}
+
+	@Test
+	void shouldHandleToolCallWithComplexJsonArguments() {
+		ToolCallback complexToolCallback = new ToolCallback() {
+			@Override
+			public ToolDefinition getToolDefinition() {
+				return DefaultToolDefinition.builder()
+					.name("complexTool")
+					.description("A tool with complex JSON input")
+					.inputSchema("{\"type\": \"object\", \"properties\": {\"nested\": {\"type\": \"object\"}}}")
+					.build();
+			}
+
+			@Override
+			public ToolMetadata getToolMetadata() {
+				return ToolMetadata.builder().build();
+			}
+
+			@Override
+			public String call(String toolInput) {
+				assertThat(toolInput).contains("nested");
+				assertThat(toolInput).contains("array");
+				return "{\"result\": \"processed\"}";
+			}
+		};
+
+		String complexJson = "{\"nested\": {\"level1\": {\"level2\": \"value\"}}, \"array\": [1, 2, 3]}";
+		AssistantMessage.ToolCall toolCall = new AssistantMessage.ToolCall("1", "function", "complexTool", complexJson);
+
+		AssistantMessage assistantMessage = AssistantMessage.builder()
+			.content("")
+			.properties(Map.of())
+			.toolCalls(List.of(toolCall))
+			.build();
+		Generation generation = new Generation(assistantMessage);
+		ChatResponse chatResponse = new ChatResponse(List.of(generation));
+
+		Prompt prompt = new Prompt(List.of(new UserMessage("test complex json")));
+
+		DefaultToolCallingManager manager = DefaultToolCallingManager.builder()
+			.observationRegistry(ObservationRegistry.NOOP)
+			.toolCallbackResolver(toolName -> "complexTool".equals(toolName) ? complexToolCallback : null)
+			.build();
+
+		assertThatNoException().isThrownBy(() -> manager.executeToolCalls(prompt, chatResponse));
+	}
+
+	@Test
+	void shouldHandleToolCallWithMalformedJson() {
+		ToolCallback toolCallback = new ToolCallback() {
+			@Override
+			public ToolDefinition getToolDefinition() {
+				return DefaultToolDefinition.builder()
+					.name("testTool")
+					.description("Test tool")
+					.inputSchema("{}")
+					.build();
+			}
+
+			@Override
+			public ToolMetadata getToolMetadata() {
+				return ToolMetadata.builder().build();
+			}
+
+			@Override
+			public String call(String toolInput) {
+				// Should still receive some input even if malformed
+				assertThat(toolInput).isNotNull();
+				return "{\"result\": \"handled\"}";
+			}
+		};
+
+		// Malformed JSON as tool arguments
+		AssistantMessage.ToolCall toolCall = new AssistantMessage.ToolCall("1", "function", "testTool",
+				"{invalid json}");
+
+		AssistantMessage assistantMessage = AssistantMessage.builder()
+			.content("")
+			.properties(Map.of())
+			.toolCalls(List.of(toolCall))
+			.build();
+		Generation generation = new Generation(assistantMessage);
+		ChatResponse chatResponse = new ChatResponse(List.of(generation));
+
+		Prompt prompt = new Prompt(List.of(new UserMessage("test malformed json")));
+
+		DefaultToolCallingManager manager = DefaultToolCallingManager.builder()
+			.observationRegistry(ObservationRegistry.NOOP)
+			.toolCallbackResolver(toolName -> "testTool".equals(toolName) ? toolCallback : null)
+			.build();
+
+		assertThatNoException().isThrownBy(() -> manager.executeToolCalls(prompt, chatResponse));
+	}
+
+	@Test
+	void shouldHandleToolCallReturningNull() {
+		ToolCallback toolCallback = new ToolCallback() {
+			@Override
+			public ToolDefinition getToolDefinition() {
+				return DefaultToolDefinition.builder()
+					.name("nullReturningTool")
+					.description("Tool that returns null")
+					.inputSchema("{}")
+					.build();
+			}
+
+			@Override
+			public ToolMetadata getToolMetadata() {
+				return ToolMetadata.builder().build();
+			}
+
+			@Override
+			public String call(String toolInput) {
+				return null; // Return null
+			}
+		};
+
+		AssistantMessage.ToolCall toolCall = new AssistantMessage.ToolCall("1", "function", "nullReturningTool", "{}");
+
+		AssistantMessage assistantMessage = AssistantMessage.builder()
+			.content("")
+			.properties(Map.of())
+			.toolCalls(List.of(toolCall))
+			.build();
+		Generation generation = new Generation(assistantMessage);
+		ChatResponse chatResponse = new ChatResponse(List.of(generation));
+
+		Prompt prompt = new Prompt(List.of(new UserMessage("test null return")));
+
+		DefaultToolCallingManager manager = DefaultToolCallingManager.builder()
+			.observationRegistry(ObservationRegistry.NOOP)
+			.toolCallbackResolver(toolName -> "nullReturningTool".equals(toolName) ? toolCallback : null)
+			.build();
+
+		assertThatNoException().isThrownBy(() -> manager.executeToolCalls(prompt, chatResponse));
+	}
+
+	@Test
+	void shouldHandleMultipleGenerationsWithToolCalls() {
+		ToolCallback toolCallback = new ToolCallback() {
+			@Override
+			public ToolDefinition getToolDefinition() {
+				return DefaultToolDefinition.builder()
+					.name("multiGenTool")
+					.description("Tool for multiple generations")
+					.inputSchema("{}")
+					.build();
+			}
+
+			@Override
+			public ToolMetadata getToolMetadata() {
+				return ToolMetadata.builder().build();
+			}
+
+			@Override
+			public String call(String toolInput) {
+				return "{\"result\": \"success\"}";
+			}
+		};
+
+		// Create multiple generations with tool calls
+		AssistantMessage.ToolCall toolCall1 = new AssistantMessage.ToolCall("1", "function", "multiGenTool", "{}");
+		AssistantMessage.ToolCall toolCall2 = new AssistantMessage.ToolCall("2", "function", "multiGenTool", "{}");
+
+		AssistantMessage assistantMessage1 = AssistantMessage.builder()
+			.content("")
+			.properties(Map.of())
+			.toolCalls(List.of(toolCall1))
+			.build();
+
+		AssistantMessage assistantMessage2 = AssistantMessage.builder()
+			.content("")
+			.properties(Map.of())
+			.toolCalls(List.of(toolCall2))
+			.build();
+
+		Generation generation1 = new Generation(assistantMessage1);
+		Generation generation2 = new Generation(assistantMessage2);
+
+		ChatResponse chatResponse = new ChatResponse(List.of(generation1, generation2));
+
+		Prompt prompt = new Prompt(List.of(new UserMessage("test multiple generations")));
+
+		DefaultToolCallingManager manager = DefaultToolCallingManager.builder()
+			.observationRegistry(ObservationRegistry.NOOP)
+			.toolCallbackResolver(toolName -> "multiGenTool".equals(toolName) ? toolCallback : null)
+			.build();
+
+		assertThatNoException().isThrownBy(() -> manager.executeToolCalls(prompt, chatResponse));
+	}
+
 }