diff --git a/mcp-core/src/main/java/io/modelcontextprotocol/client/transport/StdioClientTransport.java b/mcp-core/src/main/java/io/modelcontextprotocol/client/transport/StdioClientTransport.java
index 1b4eaca97..f5355bb29 100644
--- a/mcp-core/src/main/java/io/modelcontextprotocol/client/transport/StdioClientTransport.java
+++ b/mcp-core/src/main/java/io/modelcontextprotocol/client/transport/StdioClientTransport.java
@@ -227,16 +227,17 @@ private void handleIncomingErrors() {
 
 	@Override
 	public Mono<Void> sendMessage(JSONRPCMessage message) {
-		if (this.outboundSink.tryEmitNext(message).isSuccess()) {
-			// TODO: essentially we could reschedule ourselves in some time and make
-			// another attempt with the already read data but pause reading until
-			// success
-			// In this approach we delegate the retry and the backpressure onto the
-			// caller. This might be enough for most cases.
+		try {
+			// busyLooping retries on FAIL_NON_SERIALIZED (concurrent tryEmitNext from
+			// another thread) instead of failing immediately. The contention window is
+			// microseconds (single CAS), so the spin resolves almost instantly; the
+			// duration is just a generous upper bound for pathological cases like GC
+			// pauses.
+			this.outboundSink.emitNext(message, Sinks.EmitFailureHandler.busyLooping(Duration.ofMillis(100)));
 			return Mono.empty();
 		}
-		else {
-			return Mono.error(new RuntimeException("Failed to enqueue message"));
+		catch (Sinks.EmissionException e) {
+			return Mono.error(new RuntimeException("Failed to enqueue message", e));
 		}
 	}
 
diff --git a/mcp-core/src/test/java/io/modelcontextprotocol/client/transport/StdioClientTransportConcurrencyTest.java b/mcp-core/src/test/java/io/modelcontextprotocol/client/transport/StdioClientTransportConcurrencyTest.java
new file mode 100644
index 000000000..de70a10fd
--- /dev/null
+++ b/mcp-core/src/test/java/io/modelcontextprotocol/client/transport/StdioClientTransportConcurrencyTest.java
@@ -0,0 +1,88 @@
+/*
+ * Copyright 2024-2024 the original author or authors.
+ */
+
+package io.modelcontextprotocol.client.transport;
+
+import io.modelcontextprotocol.spec.McpSchema;
+import io.modelcontextprotocol.spec.json.gson.GsonMcpJsonMapper;
+import java.time.Duration;
+import java.util.Map;
+import java.util.concurrent.CopyOnWriteArrayList;
+import java.util.concurrent.CountDownLatch;
+import java.util.concurrent.CyclicBarrier;
+import java.util.concurrent.TimeUnit;
+import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.RepeatedTest;
+import reactor.core.publisher.Mono;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * Reproduces a race condition in StdioClientTransport.sendMessage() when two threads call
+ * it concurrently on the same transport instance.
+ *
+ * <p>
+ * The outbound sink (Sinks.many().unicast()) is wrapped by Reactor's SinkManySerialized,
+ * which uses a CAS-based guard. When two threads call tryEmitNext concurrently, the CAS
+ * loser immediately gets FAIL_NON_SERIALIZED, causing "Failed to enqueue message".
+ *
+ * <p>
+ * This occurs when an MCP server proxies concurrent tool calls to a downstream MCP server
+ * via stdio transport — each call is dispatched on a separate thread and both call
+ * sendMessage() on the same transport.
+ *
+ * @see <a href="https://github.com/modelcontextprotocol/java-sdk/issues/875">Issue
+ * #875</a>
+ */
+class StdioClientTransportConcurrencyTest {
+
+	private StdioClientTransport transport;
+
+	@AfterEach
+	void tearDown() {
+		if (transport != null) {
+			transport.closeGracefully().block(Duration.ofSeconds(5));
+		}
+	}
+
+	@RepeatedTest(20)
+	void concurrent_sendMessage_should_not_fail() throws Exception {
+		var serverParams = ServerParameters.builder("cat").env(Map.of()).build();
+		transport = new StdioClientTransport(serverParams, new GsonMcpJsonMapper());
+
+		transport.connect(mono -> mono.flatMap(msg -> Mono.empty())).block(Duration.ofSeconds(5));
+
+		var msg1 = new McpSchema.JSONRPCRequest("2.0", "tools/call", "1",
+				Map.of("name", "tool_a", "arguments", Map.of()));
+		var msg2 = new McpSchema.JSONRPCRequest("2.0", "tools/call", "2",
+				Map.of("name", "tool_b", "arguments", Map.of()));
+
+		var barrier = new CyclicBarrier(2);
+		var errors = new CopyOnWriteArrayList<Throwable>();
+		var latch = new CountDownLatch(2);
+
+		for (var msg : new McpSchema.JSONRPCMessage[] { msg1, msg2 }) {
+			new Thread(() -> {
+				try {
+					barrier.await(2, TimeUnit.SECONDS);
+					transport.sendMessage(msg).block(Duration.ofSeconds(2));
+				}
+				catch (Exception e) {
+					errors.add(e);
+				}
+				finally {
+					latch.countDown();
+				}
+			}).start();
+		}
+
+		latch.await(5, TimeUnit.SECONDS);
+
+		assertThat(errors)
+			.as("Concurrent sendMessage calls should both succeed, but the unicast sink "
+					+ "rejects one with FAIL_NON_SERIALIZED when two threads race on tryEmitNext")
+			.isEmpty();
+	}
+
+}