Add a "critical" warning tier for primary devices missing PQ keys

service/src/main/java/org/whispersystems/textsecuregcm/WhisperServerService.java

@@ -982,7 +982,7 @@ public class WhisperServerService extends Application<WhisperServerConfiguration
     webSocketEnvironment.jersey().register(new VirtualExecutorServiceProvider("managed-async-websocket-virtual-thread-"));
     webSocketEnvironment.setAuthenticator(new WebSocketAccountAuthenticator(accountAuthenticator, new AccountPrincipalSupplier(accountsManager)));
     webSocketEnvironment.setAuthenticatedWebSocketUpgradeFilter(new IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter(
-        config.idlePrimaryDeviceReminderConfiguration().minIdleDuration(), Clock.systemUTC()));
+        keysManager, config.idlePrimaryDeviceReminderConfiguration().minIdleDuration(), Clock.systemUTC()));
     webSocketEnvironment.setConnectListener(
         new AuthenticatedConnectListener(receiptSender, messagesManager, messageMetrics, pushNotificationManager,
             pushNotificationScheduler, webSocketConnectionEventManager, websocketScheduledExecutor,

service/src/main/java/org/whispersystems/textsecuregcm/auth/IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.java

@@ -6,8 +6,14 @@
 package org.whispersystems.textsecuregcm.auth;
 
 import com.google.common.annotations.VisibleForTesting;
+import io.micrometer.core.instrument.Counter;
+import io.micrometer.core.instrument.Metrics;
 import org.eclipse.jetty.websocket.server.JettyServerUpgradeRequest;
 import org.eclipse.jetty.websocket.server.JettyServerUpgradeResponse;
+import org.whispersystems.textsecuregcm.identity.IdentityType;
+import org.whispersystems.textsecuregcm.metrics.MetricsUtil;
+import org.whispersystems.textsecuregcm.storage.Device;
+import org.whispersystems.textsecuregcm.storage.KeysManager;
 import org.whispersystems.websocket.ReusableAuth;
 import org.whispersystems.websocket.auth.AuthenticatedWebSocketUpgradeFilter;
 import java.time.Clock;
@@ -17,6 +23,8 @@ import java.time.Instant;
 public class IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter implements
     AuthenticatedWebSocketUpgradeFilter<AuthenticatedDevice> {
 
+  private final KeysManager keysManager;
+
   private final Duration minIdleDuration;
   private final Clock clock;
 
@@ -26,7 +34,25 @@ public class IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter implements
   @VisibleForTesting
   static final String IDLE_PRIMARY_DEVICE_ALERT = "idle-primary-device";
 
-  public IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter(final Duration minIdleDuration, final Clock clock) {
+  @VisibleForTesting
+  static final String CRITICAL_IDLE_PRIMARY_DEVICE_ALERT = "critical-idle-primary-device";
+
+  @VisibleForTesting
+  static final Duration PQ_KEY_CHECK_THRESHOLD = Duration.ofDays(120);
+
+  private static final Counter IDLE_PRIMARY_WARNING_COUNTER = Metrics.counter(
+      MetricsUtil.name(IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.class, "idlePrimaryDeviceWarning"),
+      "critical", "false");
+
+  private static final Counter CRITICAL_IDLE_PRIMARY_WARNING_COUNTER = Metrics.counter(
+      MetricsUtil.name(IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.class, "idlePrimaryDeviceWarning"),
+      "critical", "true");
+
+  public IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter(final KeysManager keysManager,
+      final Duration minIdleDuration,
+      final Clock clock) {
+
+    this.keysManager = keysManager;
     this.minIdleDuration = minIdleDuration;
     this.clock = clock;
   }
@@ -44,8 +70,15 @@ public class IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter implements
           final Instant primaryDeviceLastSeen =
               Instant.ofEpochMilli(authenticatedDevice.getAccount().getPrimaryDevice().getLastSeen());
 
-          if (primaryDeviceLastSeen.isBefore(clock.instant().minus(minIdleDuration))) {
+          if (primaryDeviceLastSeen.isBefore(clock.instant().minus(PQ_KEY_CHECK_THRESHOLD)) &&
+              keysManager.getLastResort(authenticatedDevice.getAccount().getIdentifier(IdentityType.ACI), Device.PRIMARY_ID)
+                  .join().isEmpty()) {
+
+            response.addHeader(ALERT_HEADER, CRITICAL_IDLE_PRIMARY_DEVICE_ALERT);
+            CRITICAL_IDLE_PRIMARY_WARNING_COUNTER.increment();
+          } else if (primaryDeviceLastSeen.isBefore(clock.instant().minus(minIdleDuration))) {
             response.addHeader(ALERT_HEADER, IDLE_PRIMARY_DEVICE_ALERT);
+            IDLE_PRIMARY_WARNING_COUNTER.increment();
           }
         });
   }

service/src/test/java/org/whispersystems/textsecuregcm/auth/IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilterTest.java

@@ -5,7 +5,11 @@
 
 package org.whispersystems.textsecuregcm.auth;
 
+import static org.mockito.ArgumentMatchers.any;
+import static org.mockito.ArgumentMatchers.anyByte;
+import static org.mockito.ArgumentMatchers.eq;
 import static org.mockito.Mockito.mock;
+import static org.mockito.Mockito.never;
 import static org.mockito.Mockito.verify;
 import static org.mockito.Mockito.verifyNoInteractions;
 import static org.mockito.Mockito.when;
@@ -13,6 +17,8 @@ import static org.mockito.Mockito.when;
 import java.time.Duration;
 import java.time.Instant;
 import java.util.List;
+import java.util.Optional;
+import java.util.concurrent.CompletableFuture;
 import javax.annotation.Nullable;
 import org.eclipse.jetty.websocket.server.JettyServerUpgradeRequest;
 import org.eclipse.jetty.websocket.server.JettyServerUpgradeResponse;
@@ -20,38 +26,61 @@ import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.params.ParameterizedTest;
 import org.junit.jupiter.params.provider.Arguments;
 import org.junit.jupiter.params.provider.MethodSource;
+import org.whispersystems.textsecuregcm.entities.KEMSignedPreKey;
 import org.whispersystems.textsecuregcm.storage.Account;
 import org.whispersystems.textsecuregcm.storage.Device;
+import org.whispersystems.textsecuregcm.storage.KeysManager;
 import org.whispersystems.textsecuregcm.util.TestClock;
 import org.whispersystems.websocket.ReusableAuth;
 import org.whispersystems.websocket.auth.PrincipalSupplier;
 
 class IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilterTest {
 
+  private KeysManager keysManager;
+
   private IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter filter;
 
-  private static final Duration MIN_IDLE_DURATION = Duration.ofDays(30);
+  private static final Duration MIN_IDLE_DURATION =
+      IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.PQ_KEY_CHECK_THRESHOLD.dividedBy(2);
+
   private static final TestClock CLOCK = TestClock.pinned(Instant.now());
 
   @BeforeEach
   void setUp() {
-    filter = new IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter(MIN_IDLE_DURATION, CLOCK);
+    keysManager = mock(KeysManager.class);
+
+    filter = new IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter(keysManager, MIN_IDLE_DURATION, CLOCK);
   }
 
   @ParameterizedTest
   @MethodSource
-  void handleAuthentication(@Nullable final AuthenticatedDevice authenticatedDevice, final boolean expectAlertHeader) {
+  void handleAuthentication(@Nullable final AuthenticatedDevice authenticatedDevice,
+      final boolean primaryDeviceHasPqKeys,
+      final boolean expectPqKeyCheck,
+      @Nullable final String expectedAlertHeader) {
+
     final ReusableAuth<AuthenticatedDevice> reusableAuth = authenticatedDevice != null
         ? ReusableAuth.authenticated(authenticatedDevice, PrincipalSupplier.forImmutablePrincipal())
         : ReusableAuth.anonymous();
 
     final JettyServerUpgradeResponse response = mock(JettyServerUpgradeResponse.class);
 
+    when(keysManager.getLastResort(any(), eq(Device.PRIMARY_ID)))
+        .thenReturn(CompletableFuture.completedFuture(primaryDeviceHasPqKeys
+            ? Optional.of(mock(KEMSignedPreKey.class))
+            : Optional.empty()));
+
     filter.handleAuthentication(reusableAuth, mock(JettyServerUpgradeRequest.class), response);
 
-    if (expectAlertHeader) {
+    if (expectPqKeyCheck) {
-      verify(response).addHeader(IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.ALERT_HEADER,
+      verify(keysManager).getLastResort(any(), eq(Device.PRIMARY_ID));
-          IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.IDLE_PRIMARY_DEVICE_ALERT);
+    } else {
+      verify(keysManager, never()).getLastResort(any(), anyByte());
+    }
+
+    if (expectedAlertHeader != null) {
+      verify(response)
+          .addHeader(IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.ALERT_HEADER, expectedAlertHeader);
     } else {
       verifyNoInteractions(response);
     }
@@ -62,40 +91,70 @@ class IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilterTest {
     when(activePrimaryDevice.isPrimary()).thenReturn(true);
     when(activePrimaryDevice.getLastSeen()).thenReturn(CLOCK.millis());
 
-    final Device idlePrimaryDevice = mock(Device.class);
+    final Device minIdlePrimaryDevice = mock(Device.class);
-    when(idlePrimaryDevice.isPrimary()).thenReturn(true);
+    when(minIdlePrimaryDevice.isPrimary()).thenReturn(true);
-    when(idlePrimaryDevice.getLastSeen())
+    when(minIdlePrimaryDevice.getLastSeen())
         .thenReturn(CLOCK.instant().minus(MIN_IDLE_DURATION).minusSeconds(1).toEpochMilli());
 
+    final Device longIdlePrimaryDevice = mock(Device.class);
+    when(longIdlePrimaryDevice.isPrimary()).thenReturn(true);
+    when(longIdlePrimaryDevice.getLastSeen())
+        .thenReturn(CLOCK.instant().minus(IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.PQ_KEY_CHECK_THRESHOLD).minusSeconds(1).toEpochMilli());
+
     final Device linkedDevice = mock(Device.class);
     when(linkedDevice.isPrimary()).thenReturn(false);
 
     final Account accountWithActivePrimaryDevice = mock(Account.class);
     when(accountWithActivePrimaryDevice.getPrimaryDevice()).thenReturn(activePrimaryDevice);
 
-    final Account accountWithIdlePrimaryDevice = mock(Account.class);
+    final Account accountWithMinIdlePrimaryDevice = mock(Account.class);
-    when(accountWithIdlePrimaryDevice.getPrimaryDevice()).thenReturn(idlePrimaryDevice);
+    when(accountWithMinIdlePrimaryDevice.getPrimaryDevice()).thenReturn(minIdlePrimaryDevice);
+
+    final Account accountWithLongIdlePrimaryDevice = mock(Account.class);
+    when(accountWithLongIdlePrimaryDevice.getPrimaryDevice()).thenReturn(longIdlePrimaryDevice);
 
     return List.of(
         Arguments.argumentSet("Anonymous",
             null,
-            false),
+            true,
+            false,
+            null),
 
         Arguments.argumentSet("Authenticated as active primary device",
             new AuthenticatedDevice(accountWithActivePrimaryDevice, activePrimaryDevice),
-            false),
+            true,
+            false,
+            null),
 
         Arguments.argumentSet("Authenticated as idle primary device",
-            new AuthenticatedDevice(accountWithIdlePrimaryDevice, idlePrimaryDevice),
+            new AuthenticatedDevice(accountWithMinIdlePrimaryDevice, minIdlePrimaryDevice),
-            false),
+            true,
+            false,
+            null),
 
         Arguments.argumentSet("Authenticated as linked device with active primary device",
             new AuthenticatedDevice(accountWithActivePrimaryDevice, linkedDevice),
-            false),
+            true,
+            false,
+            null),
 
-        Arguments.argumentSet("Authenticated as linked device with idle primary device",
+        Arguments.argumentSet("Authenticated as linked device with min-idle primary device",
-            new AuthenticatedDevice(accountWithIdlePrimaryDevice, linkedDevice),
+            new AuthenticatedDevice(accountWithMinIdlePrimaryDevice, linkedDevice),
-            true)
+            true,
+            false,
+            IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.IDLE_PRIMARY_DEVICE_ALERT),
+
+        Arguments.argumentSet("Authenticated as linked device with long-idle primary device with PQ keys",
+            new AuthenticatedDevice(accountWithLongIdlePrimaryDevice, linkedDevice),
+            true,
+            true,
+            IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.IDLE_PRIMARY_DEVICE_ALERT),
+
+        Arguments.argumentSet("Authenticated as linked device with long-idle primary device without PQ keys",
+            new AuthenticatedDevice(accountWithLongIdlePrimaryDevice, linkedDevice),
+            false,
+            true,
+            IdlePrimaryDeviceAuthenticatedWebSocketUpgradeFilter.CRITICAL_IDLE_PRIMARY_DEVICE_ALERT)
     );
   }
 }