diff --git a/ts/test-electron/WebsocketResources_test.ts b/ts/test-electron/WebsocketResources_test.ts
index 63a7e66c1..06f469ee1 100644
--- a/ts/test-electron/WebsocketResources_test.ts
+++ b/ts/test-electron/WebsocketResources_test.ts
@@ -225,6 +225,20 @@ describe('WebSocket-Resource', () => {
       this.clock.next();
     });
 
+    it('optionally disconnects if suspended', function thisNeeded1(done) {
+      const socket = new FakeSocket();
+
+      sinon.stub(socket, 'close').callsFake(() => done());
+
+      new WebSocketResource(socket as WebSocket, {
+        keepalive: true,
+      });
+
+      // Just skip one hour immediately
+      this.clock.setSystemTime(NOW + 3600 * 1000);
+      this.clock.next();
+    });
+
     it('allows resetting the keepalive timer', function thisNeeded2(done) {
       const startTime = Date.now();
 
diff --git a/ts/textsecure/WebAPI.ts b/ts/textsecure/WebAPI.ts
index 5fdb6f456..c736d1b30 100644
--- a/ts/textsecure/WebAPI.ts
+++ b/ts/textsecure/WebAPI.ts
@@ -336,9 +336,18 @@ async function _connectSocket(
 
       reject(translatedError);
     });
-    client.on('connectFailed', error => {
+    client.on('connectFailed', e => {
       clearTimeout(timer);
-      reject(error);
+
+      reject(
+        makeHTTPError(
+          '_connectSocket connectFailed',
+          0,
+          {},
+          e.toString(),
+          stack
+        )
+      );
     });
   });
 }
diff --git a/ts/textsecure/WebsocketResources.ts b/ts/textsecure/WebsocketResources.ts
index d83524abd..3961d6f13 100644
--- a/ts/textsecure/WebsocketResources.ts
+++ b/ts/textsecure/WebsocketResources.ts
@@ -34,6 +34,8 @@ import { typedArrayToArrayBuffer as toArrayBuffer } from '../Crypto';
 
 import EventTarget from './EventTarget';
 
+import { isOlderThan } from '../util/timestamp';
+
 class Request {
   verb: string;
 
@@ -264,6 +266,10 @@ type KeepAliveOptionsType = {
   disconnect?: boolean;
 };
 
+const KEEPALIVE_INTERVAL_MS = 55000; // 55 seconds + 5 seconds for closing the
+// socket above.
+const MAX_KEEPALIVE_INTERVAL_MS = 300 * 1000; // 5 minutes
+
 class KeepAlive {
   private keepAliveTimer: NodeJS.Timeout | undefined;
 
@@ -275,6 +281,8 @@ class KeepAlive {
 
   private wsr: WebSocketResource;
 
+  private lastAliveAt: number = Date.now();
+
   constructor(
     websocketResource: WebSocketResource,
     opts: KeepAliveOptionsType = {}
@@ -295,9 +303,19 @@ class KeepAlive {
   public send(): void {
     this.clearTimers();
 
+    if (isOlderThan(this.lastAliveAt, MAX_KEEPALIVE_INTERVAL_MS)) {
+      window.log.info('WebSocketResources: disconnecting due to stale state');
+      this.wsr.close(
+        3001,
+        `Last keepalive request was too far in the past: ${this.lastAliveAt}`
+      );
+      return;
+    }
+
     if (this.disconnect) {
       // automatically disconnect if server doesn't ack
       this.disconnectTimer = setTimeout(() => {
+        window.log.info('WebSocketResources: disconnecting due to no response');
         this.clearTimers();
 
         this.wsr.close(3001, 'No response to keepalive request');
@@ -315,9 +333,11 @@ class KeepAlive {
   }
 
   public reset(): void {
+    this.lastAliveAt = Date.now();
+
     this.clearTimers();
 
-    this.keepAliveTimer = setTimeout(() => this.send(), 55000);
+    this.keepAliveTimer = setTimeout(() => this.send(), KEEPALIVE_INTERVAL_MS);
   }
 
   private clearTimers(): void {