diff --git a/service/src/test/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnectionTest.java b/service/src/test/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnectionTest.java
index fcd15977e..7ac63328a 100644
--- a/service/src/test/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnectionTest.java
+++ b/service/src/test/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnectionTest.java
@@ -18,6 +18,7 @@ import static org.mockito.Mockito.anyInt;
 import static org.mockito.Mockito.anyString;
 import static org.mockito.Mockito.mock;
 import static org.mockito.Mockito.never;
+import static org.mockito.Mockito.timeout;
 import static org.mockito.Mockito.times;
 import static org.mockito.Mockito.verify;
 import static org.mockito.Mockito.verifyNoMoreInteractions;
@@ -48,6 +49,7 @@ import java.util.stream.Stream;
 import org.eclipse.jetty.websocket.api.UpgradeRequest;
 import org.junit.jupiter.api.AfterEach;
 import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Disabled;
 import org.junit.jupiter.api.Test;
 import org.mockito.stubbing.Answer;
 import org.whispersystems.textsecuregcm.auth.AccountAuthenticator;
@@ -623,10 +625,19 @@ class WebSocketConnectionTest {
   }
 
   private WebSocketConnection webSocketConnection(final WebSocketClient client) {
-    return new WebSocketConnection(receiptSender, messagesManager, new MessageMetrics(),
-        mock(PushNotificationManager.class), mock(PushNotificationScheduler.class), account, device, client,
-        Schedulers.immediate(), clientReleaseManager,
-        mock(MessageDeliveryLoopMonitor.class), mock(ExperimentEnrollmentManager.class));
+    return new WebSocketConnection(receiptSender,
+        messagesManager,
+        new MessageMetrics(),
+        mock(PushNotificationManager.class),
+        mock(PushNotificationScheduler.class),
+        account,
+        device,
+        client,
+        Duration.ofMillis(100),
+        Schedulers.immediate(),
+        clientReleaseManager,
+        mock(MessageDeliveryLoopMonitor.class),
+        mock(ExperimentEnrollmentManager.class));
   }
 
   @Test
@@ -916,6 +927,40 @@ class WebSocketConnectionTest {
         .verify();
   }
 
+  @Test
+  @Disabled("Slow test")
+  public void testClientTimeout() {
+    final WebSocketClient client = mock(WebSocketClient.class);
+    final WebSocketConnection connection = webSocketConnection(client);
+
+    final UUID accountUuid = UUID.randomUUID();
+
+    when(account.getNumber()).thenReturn("+18005551234");
+    when(account.getIdentifier(IdentityType.ACI)).thenReturn(accountUuid);
+    when(device.getId()).thenReturn(Device.PRIMARY_ID);
+    when(client.isOpen()).thenReturn(true);
+
+    when(messagesManager.getMessagesForDeviceReactive(eq(accountUuid), argThat(d -> d.getId() == Device.PRIMARY_ID), anyBoolean()))
+        .thenReturn(Flux.just(createMessage(UUID.randomUUID(), UUID.randomUUID(), 1111, "first")))
+        .thenReturn(Flux.empty());
+
+    final WebSocketResponseMessage successResponse = mock(WebSocketResponseMessage.class);
+    when(successResponse.getStatus()).thenReturn(200);
+
+    when(client.sendRequest(eq("PUT"), eq("/api/v1/message"), any(), any()))
+        // This future will never complete and should time out
+        .thenAnswer(_ -> new CompletableFuture<>());
+
+    connection.start();
+
+    connection.handleNewMessageAvailable();
+
+    verify(client, timeout(30_000).times(5))
+        .sendRequest(eq("PUT"), eq("/api/v1/message"), any(), any());
+
+    verify(client, timeout(30_000)).close(eq(1011), any());
+  }
+
   private Envelope createMessage(UUID senderUuid, UUID destinationUuid, long timestamp, String content) {
     return Envelope.newBuilder()
         .setServerGuid(UUID.randomUUID().toString())