diff --git a/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractAsyncMcpToolMethodCallback.java b/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractAsyncMcpToolMethodCallback.java
index 0d7a840..5ac28ce 100644
--- a/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractAsyncMcpToolMethodCallback.java
+++ b/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractAsyncMcpToolMethodCallback.java
@@ -251,7 +251,7 @@ protected CallToolResult mapValueToCallToolResult(Object value) {
 
 		if (this.returnMode == ReturnMode.STRUCTURED) {
 			String jsonOutput = JsonParser.toJson(value);
-			Map<String, Object> structuredOutput = JsonParser.fromJson(jsonOutput, MAP_TYPE_REFERENCE);
+			Object structuredOutput = JsonParser.fromJson(jsonOutput, MAP_TYPE_REFERENCE);
 			return CallToolResult.builder().structuredContent(structuredOutput).build();
 		}
 
diff --git a/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractSyncMcpToolMethodCallback.java b/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractSyncMcpToolMethodCallback.java
index 45be3b9..b775033 100644
--- a/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractSyncMcpToolMethodCallback.java
+++ b/mcp-annotations/src/main/java/org/springaicommunity/mcp/method/tool/AbstractSyncMcpToolMethodCallback.java
@@ -162,7 +162,7 @@ protected CallToolResult processResult(Object result) {
 
 		if (this.returnMode == ReturnMode.STRUCTURED) {
 			String jsonOutput = JsonParser.toJson(result);
-			Map<String, Object> structuredOutput = JsonParser.fromJson(jsonOutput, MAP_TYPE_REFERENCE);
+			Object structuredOutput = JsonParser.fromJson(jsonOutput, Object.class);
 			return CallToolResult.builder().structuredContent(structuredOutput).build();
 		}
 
diff --git a/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncMcpToolMethodCallbackTests.java b/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncMcpToolMethodCallbackTests.java
index 724a254..6b14ed9 100644
--- a/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncMcpToolMethodCallbackTests.java
+++ b/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncMcpToolMethodCallbackTests.java
@@ -483,7 +483,7 @@ public void testConstructorParameters() {
 	}
 
 	@Test
-	public void testToolWithStructuredOutput() throws Exception {
+	public void testToolWithTextOutput() throws Exception {
 		TestToolProvider provider = new TestToolProvider();
 		Method method = TestToolProvider.class.getMethod("processObject", TestObject.class);
 		SyncMcpToolMethodCallback callback = new SyncMcpToolMethodCallback(ReturnMode.TEXT, method, provider);
@@ -546,6 +546,28 @@ public void testToolReturningComplexListObject() throws Exception {
 				[{"name":"test","value":42}]"""));
 	}
 
+	@Test
+	public void testToolReturningStructuredComplexListObject() throws Exception {
+		TestToolProvider provider = new TestToolProvider();
+		Method method = TestToolProvider.class.getMethod("returnListObjectTool", String.class, int.class);
+		SyncMcpToolMethodCallback callback = new SyncMcpToolMethodCallback(ReturnMode.STRUCTURED, method, provider);
+
+		McpSyncServerExchange exchange = mock(McpSyncServerExchange.class);
+		CallToolRequest request = new CallToolRequest("return-list-object-tool", Map.of("name", "test", "value", 42));
+
+		CallToolResult result = callback.apply(exchange, request);
+
+		assertThat(result).isNotNull();
+		assertThat(result.isError()).isFalse();
+
+		assertThat(result.structuredContent()).isNotNull();
+		assertThat(result.structuredContent()).isInstanceOf(List.class);
+		assertThat((List<?>) result.structuredContent()).hasSize(1);
+		Map<String, Object> firstEntry = ((List<Map<String, Object>>) result.structuredContent()).get(0);
+		assertThat(firstEntry).containsEntry("name", "test");
+		assertThat(firstEntry).containsEntry("value", 42);
+	}
+
 	@Test
 	public void testToolReturningStringList() throws Exception {
 		TestToolProvider provider = new TestToolProvider();
diff --git a/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncStatelessMcpToolMethodCallbackTests.java b/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncStatelessMcpToolMethodCallbackTests.java
index e1e066e..b1ea1f8 100644
--- a/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncStatelessMcpToolMethodCallbackTests.java
+++ b/mcp-annotations/src/test/java/org/springaicommunity/mcp/method/tool/SyncStatelessMcpToolMethodCallbackTests.java
@@ -10,6 +10,7 @@
 import java.util.Map;
 
 import io.modelcontextprotocol.common.McpTransportContext;
+import io.modelcontextprotocol.server.McpSyncServerExchange;
 import io.modelcontextprotocol.spec.McpSchema.CallToolRequest;
 import io.modelcontextprotocol.spec.McpSchema.CallToolResult;
 import io.modelcontextprotocol.spec.McpSchema.TextContent;
@@ -128,6 +129,11 @@ public String toolWithContextAndRequest(McpTransportContext context, CallToolReq
 			return "Context present, Tool: " + request.name();
 		}
 
+		@McpTool(name = "return-list-object-tool", description = "Tool that returns a list of complex objects")
+		public List<TestObject> returnListObjectTool(String name, int value) {
+			return List.of(new TestObject(name, value));
+		}
+
 		/**
 		 * Tool with McpMeta parameter
 		 */
@@ -543,6 +549,28 @@ public void testToolReturningComplexObject() throws Exception {
 		assertThat((Map<String, Object>) result.structuredContent()).containsEntry("value", 42);
 	}
 
+	@Test
+	public void testToolReturningStructuredComplexListObject() throws Exception {
+		TestToolProvider provider = new TestToolProvider();
+		Method method = TestToolProvider.class.getMethod("returnListObjectTool", String.class, int.class);
+		SyncMcpToolMethodCallback callback = new SyncMcpToolMethodCallback(ReturnMode.STRUCTURED, method, provider);
+
+		McpSyncServerExchange exchange = mock(McpSyncServerExchange.class);
+		CallToolRequest request = new CallToolRequest("return-list-object-tool", Map.of("name", "test", "value", 42));
+
+		CallToolResult result = callback.apply(exchange, request);
+
+		assertThat(result).isNotNull();
+		assertThat(result.isError()).isFalse();
+
+		assertThat(result.structuredContent()).isNotNull();
+		assertThat(result.structuredContent()).isInstanceOf(List.class);
+		assertThat((List<?>) result.structuredContent()).hasSize(1);
+		Map<String, Object> firstEntry = ((List<Map<String, Object>>) result.structuredContent()).get(0);
+		assertThat(firstEntry).containsEntry("name", "test");
+		assertThat(firstEntry).containsEntry("value", 42);
+	}
+
 	@Test
 	public void testVoidReturnMode() throws Exception {
 		TestToolProvider provider = new TestToolProvider();
diff --git a/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncMcpToolProviderTests.java b/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncMcpToolProviderTests.java
index aa94635..812daa7 100644
--- a/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncMcpToolProviderTests.java
+++ b/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncMcpToolProviderTests.java
@@ -693,6 +693,47 @@ public List<CustomResult> listResponseTool(String input) {
 				[{"message":"Processed: test"}]"""));
 	}
 
+	@Test
+	void testToolWithStructuredListReturnType() {
+
+		record CustomResult(String message) {
+		}
+
+		class ListResponseTool {
+
+			@McpTool(name = "list-response", description = "Tool List response", generateOutputSchema = true)
+			public List<CustomResult> listResponseTool(String input) {
+				return List.of(new CustomResult("Processed: " + input));
+			}
+
+		}
+
+		ListResponseTool toolObject = new ListResponseTool();
+		SyncMcpToolProvider provider = new SyncMcpToolProvider(List.of(toolObject));
+
+		List<SyncToolSpecification> toolSpecs = provider.getToolSpecifications();
+
+		assertThat(toolSpecs).hasSize(1);
+		SyncToolSpecification toolSpec = toolSpecs.get(0);
+
+		assertThat(toolSpec.tool().name()).isEqualTo("list-response");
+		assertThat(toolSpec.tool().outputSchema()).isNotNull();
+
+		BiFunction<McpSyncServerExchange, CallToolRequest, McpSchema.CallToolResult> callHandler = toolSpec
+			.callHandler();
+
+		McpSchema.CallToolResult result = callHandler.apply(mock(McpSyncServerExchange.class),
+				new CallToolRequest("list-response", Map.of("input", "test")));
+
+		assertThat(result).isNotNull();
+		assertThat(result.isError()).isFalse();
+
+		assertThat(result.structuredContent()).isInstanceOf(List.class);
+		assertThat((List<?>) result.structuredContent()).hasSize(1);
+		Map<String, Object> firstEntry = ((List<Map<String, Object>>) result.structuredContent()).get(0);
+		assertThat(firstEntry).containsEntry("message", "Processed: test");
+	}
+
 	@Test
 	void testToolWithPrimitiveReturnTypeNoOutputSchema() {
 		class PrimitiveTool {
diff --git a/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncStatelessMcpToolProviderTests.java b/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncStatelessMcpToolProviderTests.java
index 58bfe82..7af35f8 100644
--- a/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncStatelessMcpToolProviderTests.java
+++ b/mcp-annotations/src/test/java/org/springaicommunity/mcp/provider/tool/SyncStatelessMcpToolProviderTests.java
@@ -692,6 +692,46 @@ public List<CustomResult> listResponseTool(String input) {
 				[{"message":"Processed: test"}]"""));
 	}
 
+	@Test
+	void testToolWithStructuredListReturnType() {
+
+		record CustomResult(String message) {
+		}
+
+		class ListResponseTool {
+
+			@McpTool(name = "list-response", description = "Tool List response", generateOutputSchema = true)
+			public List<CustomResult> listResponseTool(String input) {
+				return List.of(new CustomResult("Processed: " + input));
+			}
+
+		}
+
+		ListResponseTool toolObject = new ListResponseTool();
+		SyncStatelessMcpToolProvider provider = new SyncStatelessMcpToolProvider(List.of(toolObject));
+
+		List<SyncToolSpecification> toolSpecs = provider.getToolSpecifications();
+
+		assertThat(toolSpecs).hasSize(1);
+		SyncToolSpecification toolSpec = toolSpecs.get(0);
+
+		assertThat(toolSpec.tool().name()).isEqualTo("list-response");
+		assertThat(toolSpec.tool().outputSchema()).isNotNull();
+
+		BiFunction<McpTransportContext, CallToolRequest, McpSchema.CallToolResult> callHandler = toolSpec.callHandler();
+
+		McpSchema.CallToolResult result = callHandler.apply(mock(McpTransportContext.class),
+				new CallToolRequest("list-response", Map.of("input", "test")));
+
+		assertThat(result).isNotNull();
+		assertThat(result.isError()).isFalse();
+
+		assertThat(result.structuredContent()).isInstanceOf(List.class);
+		assertThat((List<?>) result.structuredContent()).hasSize(1);
+		Map<String, Object> firstEntry = ((List<Map<String, Object>>) result.structuredContent()).get(0);
+		assertThat(firstEntry).containsEntry("message", "Processed: test");
+	}
+
 	@Test
 	void testToolWithPrimitiveReturnTypeNoOutputSchema() {
 		class PrimitiveTool {