diff --git a/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProvider.java b/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProvider.java
index a8d5ea451c..621e45da30 100644
--- a/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProvider.java
+++ b/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProvider.java
@@ -17,6 +17,7 @@
 package org.springframework.ai.mcp.annotation.provider.tool;
 
 import java.lang.reflect.Method;
+import java.lang.reflect.ParameterizedType;
 import java.util.Comparator;
 import java.util.List;
 import java.util.function.BiFunction;
@@ -127,12 +128,16 @@ public List<AsyncToolSpecification> getToolSpecifications() {
 							&& !ReactiveUtils.isReactiveReturnTypeOfCallToolResult(mcpToolMethod)) {
 
 						ReactiveUtils.getReactiveReturnTypeArgument(mcpToolMethod).ifPresent(typeArgument -> {
-							Class<?> methodReturnType = typeArgument instanceof Class<?> ? (Class<?>) typeArgument
-									: null;
-							if (!ClassUtils.isPrimitiveOrWrapper(methodReturnType)
-									&& !ClassUtils.isSimpleValueType(methodReturnType)) {
+							if (typeArgument instanceof Class<?> methodReturnType) {
+								if (!ClassUtils.isPrimitiveOrWrapper(methodReturnType)
+										&& !ClassUtils.isSimpleValueType(methodReturnType)) {
+									toolBuilder.outputSchema(this.getJsonMapper(),
+											McpJsonSchemaGenerator.generateFromClass(methodReturnType));
+								}
+							}
+							else if (typeArgument instanceof ParameterizedType) {
 								toolBuilder.outputSchema(this.getJsonMapper(),
-										McpJsonSchemaGenerator.generateFromClass((Class<?>) typeArgument));
+										McpJsonSchemaGenerator.generateFromType(typeArgument));
 							}
 						});
 					}
diff --git a/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProvider.java b/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProvider.java
index d64aad551a..7de44508d1 100644
--- a/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProvider.java
+++ b/mcp/mcp-annotations/src/main/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProvider.java
@@ -17,6 +17,7 @@
 package org.springframework.ai.mcp.annotation.provider.tool;
 
 import java.lang.reflect.Method;
+import java.lang.reflect.ParameterizedType;
 import java.util.Comparator;
 import java.util.List;
 import java.util.function.BiFunction;
@@ -132,10 +133,14 @@ public List<AsyncToolSpecification> getToolSpecifications() {
 							&& !ReactiveUtils.isReactiveReturnTypeOfCallToolResult(mcpToolMethod)) {
 
 						ReactiveUtils.getReactiveReturnTypeArgument(mcpToolMethod).ifPresent(typeArgument -> {
-							Class<?> methodReturnType = typeArgument instanceof Class<?> ? (Class<?>) typeArgument
-									: null;
-							if (!ClassUtils.isPrimitiveOrWrapper(methodReturnType)
-									&& !ClassUtils.isSimpleValueType(methodReturnType)) {
+							if (typeArgument instanceof Class<?> methodReturnType) {
+								if (!ClassUtils.isPrimitiveOrWrapper(methodReturnType)
+										&& !ClassUtils.isSimpleValueType(methodReturnType)) {
+									toolBuilder.outputSchema(this.getJsonMapper(),
+											McpJsonSchemaGenerator.generateFromClass(methodReturnType));
+								}
+							}
+							else if (typeArgument instanceof ParameterizedType) {
 								toolBuilder.outputSchema(this.getJsonMapper(),
 										McpJsonSchemaGenerator.generateFromType(typeArgument));
 							}
diff --git a/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProviderTests.java b/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProviderTests.java
index 81a74f2205..7dd1045a97 100644
--- a/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProviderTests.java
+++ b/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncMcpToolProviderTests.java
@@ -917,6 +917,42 @@ public Mono<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 Mono<List<CustomResult>> listResponseTool(String input) {
+				return Mono.just(List.of(new CustomResult("Processed: " + input)));
+			}
+
+		}
+
+		AsyncMcpToolProvider provider = new AsyncMcpToolProvider(List.of(new ListResponseTool()));
+
+		List<AsyncToolSpecification> toolSpecs = provider.getToolSpecifications();
+
+		assertThat(toolSpecs).hasSize(1);
+		AsyncToolSpecification toolSpec = toolSpecs.get(0);
+		assertThat(toolSpec.tool().outputSchema()).containsEntry("type", "array").containsKey("items");
+		assertThat(toolSpec.tool().outputSchema().toString()).contains("message");
+
+		Mono<CallToolResult> result = toolSpec.callHandler()
+			.apply(mock(McpAsyncServerExchange.class),
+					CallToolRequest.builder("list-response").arguments(Map.of("input", "test")).build());
+
+		StepVerifier.create(result).assertNext(callToolResult -> {
+			assertThat(callToolResult.isError()).isFalse();
+			assertThat(callToolResult.structuredContent()).isInstanceOf(List.class);
+			assertThat((List<?>) callToolResult.structuredContent()).singleElement()
+				.isInstanceOfSatisfying(Map.class,
+						item -> assertThat(item).containsEntry("message", "Processed: test"));
+		}).verifyComplete();
+	}
+
 	@Test
 	void testToolWithFluxReturnType() {
 
diff --git a/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProviderTests.java b/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProviderTests.java
index d09ceaef9e..0df5f17c8e 100644
--- a/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProviderTests.java
+++ b/mcp/mcp-annotations/src/test/java/org/springframework/ai/mcp/annotation/provider/tool/AsyncStatelessMcpToolProviderTests.java
@@ -952,6 +952,42 @@ public Mono<CustomResult> noOutputSchemaTool(String input) {
 		assertThat(toolSpec.tool().outputSchema()).isNull();
 	}
 
+	@Test
+	void testToolWithStructuredListReturnType() {
+		record CustomResult(String message) {
+		}
+
+		class ListResponseTool {
+
+			@McpTool(name = "list-response", description = "Tool List response", generateOutputSchema = true)
+			public Mono<List<CustomResult>> listResponseTool(String input) {
+				return Mono.just(List.of(new CustomResult("Processed: " + input)));
+			}
+
+		}
+
+		AsyncStatelessMcpToolProvider provider = new AsyncStatelessMcpToolProvider(List.of(new ListResponseTool()));
+
+		List<AsyncToolSpecification> toolSpecs = provider.getToolSpecifications();
+
+		assertThat(toolSpecs).hasSize(1);
+		AsyncToolSpecification toolSpec = toolSpecs.get(0);
+		assertThat(toolSpec.tool().outputSchema()).containsEntry("type", "array").containsKey("items");
+		assertThat(toolSpec.tool().outputSchema().toString()).contains("message");
+
+		Mono<CallToolResult> result = toolSpec.callHandler()
+			.apply(mock(McpTransportContext.class),
+					CallToolRequest.builder("list-response").arguments(Map.of("input", "test")).build());
+
+		StepVerifier.create(result).assertNext(callToolResult -> {
+			assertThat(callToolResult.isError()).isFalse();
+			assertThat(callToolResult.structuredContent()).isInstanceOf(List.class);
+			assertThat((List<?>) callToolResult.structuredContent()).singleElement()
+				.isInstanceOfSatisfying(Map.class,
+						item -> assertThat(item).containsEntry("message", "Processed: test"));
+		}).verifyComplete();
+	}
+
 	@Test
 	void testGetToolSpecificationsWithOutputSchemaGeneration() {
 		// Helper class for complex return type