Add (failing) test for send message timeouts

service/src/test/java/org/whispersystems/textsecuregcm/websocket/WebSocketConnectionIntegrationTest.java

@@ -33,7 +33,6 @@ import java.util.concurrent.Executors;
 import java.util.concurrent.ScheduledExecutorService;
 import java.util.concurrent.TimeUnit;
 import java.util.concurrent.atomic.AtomicBoolean;
-import java.util.stream.Collectors;
 import org.apache.commons.lang3.RandomStringUtils;
 import org.junit.jupiter.api.AfterEach;
 import org.junit.jupiter.api.BeforeEach;
@@ -243,8 +242,91 @@ class WebSocketConnectionIntegrationTest {
             } catch (InvalidProtocolBufferException e) {
               throw new RuntimeException(e);
             }
-          })
+          }).toList();
-          .collect(Collectors.toList());
+
+      assertTrue(expectedMessages.containsAll(sentMessages));
+    });
+  }
+
+  @Test
+  void testProcessStoredMessagesSendFutureTimeout() {
+    final int persistedMessageCount = 207;
+    final int cachedMessageCount = 173;
+
+    final List<MessageProtos.Envelope> expectedMessages = new ArrayList<>(persistedMessageCount + cachedMessageCount);
+
+    assertTimeoutPreemptively(Duration.ofSeconds(15), () -> {
+
+      {
+        final List<MessageProtos.Envelope> persistedMessages = new ArrayList<>(persistedMessageCount);
+
+        for (int i = 0; i < persistedMessageCount; i++) {
+          final MessageProtos.Envelope envelope = generateRandomMessage(UUID.randomUUID());
+          persistedMessages.add(envelope);
+          expectedMessages.add(envelope);
+        }
+
+        messagesDynamoDb.store(persistedMessages, account.getUuid(), device.getId());
+      }
+
+      for (int i = 0; i < cachedMessageCount; i++) {
+        final UUID messageGuid = UUID.randomUUID();
+        final MessageProtos.Envelope envelope = generateRandomMessage(messageGuid);
+        messagesCache.insert(messageGuid, account.getUuid(), device.getId(), envelope);
+
+        expectedMessages.add(envelope);
+      }
+
+      final WebSocketResponseMessage successResponse = mock(WebSocketResponseMessage.class);
+      when(successResponse.getStatus()).thenReturn(200);
+
+      final CompletableFuture<WebSocketResponseMessage> neverCompleting = new CompletableFuture<>();
+
+      // for the first message, return a future that never completes
+      when(webSocketClient.sendRequest(eq("PUT"), eq("/api/v1/message"), anyList(), any()))
+          .thenReturn(neverCompleting)
+          .thenReturn(CompletableFuture.completedFuture(successResponse));
+
+      when(webSocketClient.isOpen()).thenReturn(true);
+
+      final AtomicBoolean queueCleared = new AtomicBoolean(false);
+
+      when(webSocketClient.sendRequest(eq("PUT"), eq("/api/v1/queue/empty"), anyList(), any())).thenAnswer(
+          (Answer<CompletableFuture<WebSocketResponseMessage>>) invocation -> {
+            synchronized (queueCleared) {
+              queueCleared.set(true);
+              queueCleared.notifyAll();
+            }
+
+            return CompletableFuture.completedFuture(successResponse);
+          });
+
+      webSocketConnection.processStoredMessages();
+
+      synchronized (queueCleared) {
+        while (!queueCleared.get()) {
+          queueCleared.wait();
+        }
+      }
+
+      //noinspection unchecked
+      ArgumentCaptor<Optional<byte[]>> messageBodyCaptor = ArgumentCaptor.forClass(Optional.class);
+
+      // We expect all of the messages from both pools to be sent, plus one for the future that times out
+      verify(webSocketClient, atMost(persistedMessageCount + cachedMessageCount + 1)).sendRequest(eq("PUT"),
+          eq("/api/v1/message"), anyList(), messageBodyCaptor.capture());
+
+      verify(webSocketClient).sendRequest(eq("PUT"), eq("/api/v1/queue/empty"), anyList(), eq(Optional.empty()));
+
+      final List<MessageProtos.Envelope> sentMessages = messageBodyCaptor.getAllValues().stream()
+          .map(Optional::get)
+          .map(messageBytes -> {
+            try {
+              return Envelope.parseFrom(messageBytes);
+            } catch (InvalidProtocolBufferException e) {
+              throw new RuntimeException(e);
+            }
+          }).toList();
 
       assertTrue(expectedMessages.containsAll(sentMessages));
     });