diff --git a/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java b/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
index 147f62cff..887a91ff6 100644
--- a/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
+++ b/service/src/main/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnection.java
@@ -26,6 +26,7 @@ import java.util.concurrent.ScheduledExecutorService;
 import java.util.concurrent.ScheduledFuture;
 import java.util.concurrent.Semaphore;
 import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
 import java.util.concurrent.atomic.AtomicBoolean;
 import java.util.concurrent.atomic.AtomicInteger;
 import java.util.concurrent.atomic.AtomicLong;
@@ -84,8 +85,11 @@ public class WebSocketConnection implements MessageAvailabilityListener, Displac
       "messageAvailableAfterClientClosed");
   private static final String SEND_MESSAGES_FLUX_NAME = MetricsUtil.name(WebSocketConnection.class,
       "sendMessages");
+  private static final String SEND_MESSAGE_TIMEOUT_COUNTER = MetricsUtil.name(WebSocketConnection.class,
+      "sendMessageTimeout");
   private static final String STATUS_CODE_TAG = "status";
   private static final String STATUS_MESSAGE_TAG = "message";
+  private static final String ERROR_TYPE_TAG = "errorType";
   private static final String REACTIVE_TAG = "reactive";
 
   private static final long SLOW_DRAIN_THRESHOLD = 10_000;
@@ -426,7 +430,22 @@ public class WebSocketConnection implements MessageAvailabilityListener, Displac
         .metrics()
         .limitRate(MESSAGE_PUBLISHER_LIMIT_RATE)
         .flatMapSequential(envelope ->
-            Mono.fromFuture(sendMessage(envelope).orTimeout(sendFuturesTimeoutMillis, TimeUnit.MILLISECONDS)))
+            Mono.fromFuture(sendMessage(envelope)
+                    .orTimeout(sendFuturesTimeoutMillis, TimeUnit.MILLISECONDS))
+                .doOnError(e -> {
+                  final String errorType;
+                  if (!(e instanceof TimeoutException)) {
+                    // TimeoutExceptions are expected, no need to log
+                    logger.warn("Send message failed", e);
+                    errorType = "other";
+                  } else {
+                    errorType = "timeout";
+                  }
+                  final Tags tags = Tags.of(
+                      UserAgentTagUtil.getPlatformTag(client.getUserAgent()),
+                      Tag.of(ERROR_TYPE_TAG, errorType));
+                  Metrics.counter(SEND_MESSAGE_TIMEOUT_COUNTER, tags).increment();
+                }))
         .doOnError(queueCleared::completeExceptionally)
         .doOnComplete(() -> queueCleared.complete(null))
         .subscribeOn(reactiveScheduler)