diff --git a/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpClientSession.java b/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpClientSession.java
index 3d7154278..808b1940b 100644
--- a/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpClientSession.java
+++ b/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpClientSession.java
@@ -264,21 +264,25 @@ public <T> Mono<T> sendRequest(String method, Object requestParams, TypeRef<T> t
 				this.pendingResponses.remove(requestId);
 				pendingResponseSink.error(error);
 			});
-		})).timeout(this.requestTimeout).handle((jsonRpcResponse, deliveredResponseSink) -> {
-			if (jsonRpcResponse.error() != null) {
-				logger.info("Server returned a JSON-RPC error when calling method {}: {}", method,
-						jsonRpcResponse.error());
-				deliveredResponseSink.error(new McpError(jsonRpcResponse.error()));
-			}
-			else {
-				if (typeRef.getType().equals(Void.class)) {
-					deliveredResponseSink.complete();
+		}))
+			.timeout(this.requestTimeout)
+			.doOnError(e -> this.pendingResponses.remove(requestId))
+			.doOnCancel(() -> this.pendingResponses.remove(requestId))
+			.handle((jsonRpcResponse, deliveredResponseSink) -> {
+				if (jsonRpcResponse.error() != null) {
+					logger.info("Server returned a JSON-RPC error when calling method {}: {}", method,
+							jsonRpcResponse.error());
+					deliveredResponseSink.error(new McpError(jsonRpcResponse.error()));
 				}
 				else {
-					deliveredResponseSink.next(this.transport.unmarshalFrom(jsonRpcResponse.result(), typeRef));
+					if (typeRef.getType().equals(Void.class)) {
+						deliveredResponseSink.complete();
+					}
+					else {
+						deliveredResponseSink.next(this.transport.unmarshalFrom(jsonRpcResponse.result(), typeRef));
+					}
 				}
-			}
-		});
+			});
 	}
 
 	/**
diff --git a/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpServerSession.java b/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpServerSession.java
index 8f86138f0..587000c30 100644
--- a/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpServerSession.java
+++ b/mcp-core/src/main/java/io/modelcontextprotocol/spec/McpServerSession.java
@@ -184,19 +184,23 @@ public <T> Mono<T> sendRequest(String method, Object requestParams, TypeRef<T> t
 				this.pendingResponses.remove(requestId);
 				sink.error(error);
 			});
-		}).timeout(requestTimeout).handle((jsonRpcResponse, sink) -> {
-			if (jsonRpcResponse.error() != null) {
-				sink.error(new McpError(jsonRpcResponse.error()));
-			}
-			else {
-				if (typeRef.getType().equals(Void.class)) {
-					sink.complete();
+		})
+			.timeout(requestTimeout)
+			.doOnError(e -> this.pendingResponses.remove(requestId))
+			.doOnCancel(() -> this.pendingResponses.remove(requestId))
+			.handle((jsonRpcResponse, sink) -> {
+				if (jsonRpcResponse.error() != null) {
+					sink.error(new McpError(jsonRpcResponse.error()));
 				}
 				else {
-					sink.next(this.transport.unmarshalFrom(jsonRpcResponse.result(), typeRef));
+					if (typeRef.getType().equals(Void.class)) {
+						sink.complete();
+					}
+					else {
+						sink.next(this.transport.unmarshalFrom(jsonRpcResponse.result(), typeRef));
+					}
 				}
-			}
-		});
+			});
 	}
 
 	@Override
diff --git a/mcp-core/src/test/java/io/modelcontextprotocol/spec/McpClientSessionTests.java b/mcp-core/src/test/java/io/modelcontextprotocol/spec/McpClientSessionTests.java
index ae5daf1f4..a2ab5e8c5 100644
--- a/mcp-core/src/test/java/io/modelcontextprotocol/spec/McpClientSessionTests.java
+++ b/mcp-core/src/test/java/io/modelcontextprotocol/spec/McpClientSessionTests.java
@@ -303,4 +303,22 @@ void testGracefulShutdown() {
 		StepVerifier.create(session.closeGracefully()).verifyComplete();
 	}
 
+	@Test
+	void testRequestTimeoutRemovesPendingResponse() throws Exception {
+		var transport = new MockMcpClientTransport();
+		var session = new McpClientSession(Duration.ofMillis(50), transport, Map.of(), Map.of(), Function.identity());
+
+		Mono<String> responseMono = session.sendRequest(TEST_METHOD, "test", responseType);
+
+		StepVerifier.create(responseMono).expectError(java.util.concurrent.TimeoutException.class).verify();
+
+		var field = McpClientSession.class.getDeclaredField("pendingResponses");
+		field.setAccessible(true);
+		@SuppressWarnings("unchecked")
+		var pendingResponses = (java.util.Map<Object, ?>) field.get(session);
+		assertThat(pendingResponses).isEmpty();
+
+		session.close();
+	}
+
 }