diff --git a/src/main/java/org/sonarsource/sonarqube/mcp/client/ManagedStdioClientTransport.java b/src/main/java/org/sonarsource/sonarqube/mcp/client/ManagedStdioClientTransport.java
index 43781f7b..774078b7 100644
--- a/src/main/java/org/sonarsource/sonarqube/mcp/client/ManagedStdioClientTransport.java
+++ b/src/main/java/org/sonarsource/sonarqube/mcp/client/ManagedStdioClientTransport.java
@@ -139,9 +139,15 @@ private void handleIncomingErrors() {
 
   @Override
   public Mono<Void> sendMessage(McpSchema.JSONRPCMessage message) {
-    return outboundSink.tryEmitNext(message).isSuccess() 
-      ? Mono.empty() 
-      : Mono.error(new RuntimeException("Failed to enqueue message for '" + serverName + "'"));
+    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 an upper bound.
+      outboundSink.emitNext(message, Sinks.EmitFailureHandler.busyLooping(Duration.ofMillis(100)));
+      return Mono.empty();
+    } catch (Sinks.EmissionException e) {
+      return Mono.error(new RuntimeException("Failed to enqueue message for '" + serverName + "'", e));
+    }
   }
 
   private void startInboundProcessing() {
diff --git a/src/test/java/org/sonarsource/sonarqube/mcp/client/ManagedStdioClientTransportConcurrencyTest.java b/src/test/java/org/sonarsource/sonarqube/mcp/client/ManagedStdioClientTransportConcurrencyTest.java
new file mode 100644
index 00000000..cdfa833c
--- /dev/null
+++ b/src/test/java/org/sonarsource/sonarqube/mcp/client/ManagedStdioClientTransportConcurrencyTest.java
@@ -0,0 +1,121 @@
+/*
+ * SonarQube MCP Server
+ * Copyright (C) 2025 SonarSource
+ * mailto:info AT sonarsource DOT com
+ *
+ * This program is free software; you can redistribute it and/or
+ * modify it under the terms of the Sonar Source-Available License Version 1, as published by SonarSource Sàrl.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.
+ * See the Sonar Source-Available License for more details.
+ *
+ * You should have received a copy of the Sonar Source-Available License
+ * along with this program; if not, see https://sonarsource.com/license/ssal/
+ */
+package org.sonarsource.sonarqube.mcp.client;
+
+import io.modelcontextprotocol.client.transport.ServerParameters;
+import io.modelcontextprotocol.spec.McpSchema;
+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 org.sonarsource.sonarqube.mcp.transport.McpJsonMappers;
+import reactor.core.publisher.Mono;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+/**
+ * Reproduces the concurrent sendMessage bug in ManagedStdioClientTransport.
+ *
+ * <p>When two threads call sendMessage simultaneously on the same transport,
+ * the unicast Reactor sink rejects the second emit with FAIL_NON_SERIALIZED,
+ * surfacing as "Failed to enqueue message for 'sonar-cag'".
+ *
+ * <p>This matches the production failure observed when an MCP client sends two
+ * parallel tool calls (e.g., get_current_architecture with depth=0 and depth=1),
+ * which are dispatched on separate boundedElastic threads that race on the same transport.
+ */
+class ManagedStdioClientTransportConcurrencyTest {
+
+  private ManagedStdioClientTransport transport;
+
+  @AfterEach
+  void tearDown() {
+    if (transport != null) {
+      transport.closeGracefully().block(Duration.ofSeconds(5));
+    }
+  }
+
+  /**
+   * Reproduces the exact production scenario: two concurrent tool calls through
+   * the same transport. The unicast sink's CAS-based serialization guard causes
+   * one of the two tryEmitNext calls to return FAIL_NON_SERIALIZED.
+   *
+   * Repeated 20 times because the race is timing-dependent.
+   */
+  @RepeatedTest(20)
+  void concurrent_sendMessage_should_not_fail() throws Exception {
+    // Use 'cat' as a simple process that keeps stdin/stdout open
+    var serverParams = ServerParameters.builder("cat")
+      .env(Map.of())
+      .build();
+    transport = new ManagedStdioClientTransport("test-server", serverParams, McpJsonMappers.DEFAULT);
+
+    // Connect the transport (starts process, sets up sinks and processing threads)
+    transport.connect(mono -> mono.flatMap(msg -> Mono.empty())).block(Duration.ofSeconds(5));
+
+    // Two JSON-RPC messages mimicking two concurrent tool calls
+    var msg1 = new McpSchema.JSONRPCRequest("2.0", "tools/call", "1",
+      Map.of("name", "get_current_architecture", "arguments", Map.of("depth", 0)));
+    var msg2 = new McpSchema.JSONRPCRequest("2.0", "tools/call", "2",
+      Map.of("name", "get_current_architecture", "arguments", Map.of("depth", 1)));
+
+    // CyclicBarrier maximizes chance of concurrent execution
+    var barrier = new CyclicBarrier(2);
+    var errors = new CopyOnWriteArrayList<Throwable>();
+    var latch = new CountDownLatch(2);
+
+    Runnable sender1 = () -> {
+      try {
+        barrier.await(2, TimeUnit.SECONDS);
+        transport.sendMessage(msg1).block(Duration.ofSeconds(2));
+      } catch (Exception e) {
+        errors.add(e);
+      } finally {
+        latch.countDown();
+      }
+    };
+
+    Runnable sender2 = () -> {
+      try {
+        barrier.await(2, TimeUnit.SECONDS);
+        transport.sendMessage(msg2).block(Duration.ofSeconds(2));
+      } catch (Exception e) {
+        errors.add(e);
+      } finally {
+        latch.countDown();
+      }
+    };
+
+    var t1 = new Thread(sender1, "boundedElastic-5");
+    var t2 = new Thread(sender2, "boundedElastic-6");
+    t1.start();
+    t2.start();
+
+    latch.await(5, TimeUnit.SECONDS);
+
+    // With the unicast sink, one send fails with "Failed to enqueue message"
+    // due to FAIL_NON_SERIALIZED when the two tryEmitNext calls overlap.
+    assertThat(errors)
+      .as("Both concurrent sendMessage calls should succeed, but the unicast sink " +
+        "rejects one with FAIL_NON_SERIALIZED when two threads race on tryEmitNext")
+      .isEmpty();
+  }
+}