diff --git a/chrome/browser/chromeos/android_sms/connection_manager.cc b/chrome/browser/chromeos/android_sms/connection_manager.cc
index 34b8039cf2f0..2243adbd47c6 100644
--- a/chrome/browser/chromeos/android_sms/connection_manager.cc
+++ b/chrome/browser/chromeos/android_sms/connection_manager.cc
@@ -138,6 +138,8 @@ void ConnectionManager::UpdateConnectionStatus() {
     connection_establisher_->TearDownConnection(
         *enabled_pwa_url_, GetCurrentServiceWorkerContext());
     GetCurrentServiceWorkerContext()->RemoveObserver(this);
+    active_version_id_.reset();
+    prev_active_version_id_.reset();
   }
 
   enabled_pwa_url_ = updated_pwa_url;
diff --git a/chrome/browser/chromeos/android_sms/connection_manager_unittest.cc b/chrome/browser/chromeos/android_sms/connection_manager_unittest.cc
index 0380ae7dc483..e227c0569576 100644
--- a/chrome/browser/chromeos/android_sms/connection_manager_unittest.cc
+++ b/chrome/browser/chromeos/android_sms/connection_manager_unittest.cc
@@ -306,6 +306,11 @@ TEST_F(ConnectionManagerTest, FeatureStateChange) {
   // Verify that enabling feature establishes connection again.
   SetPwaState(PwaState::kEnabledWithNewUrl);
   VerifyEstablishConnectionCalls(3u /* expected_count */);
+
+  // Verify that connection is established if the version id changes.
+  fake_new_service_worker_context()->NotifyObserversOnNoControllees(
+      kDummyVersionId2, GetAndroidMessagesURL());
+  VerifyEstablishConnectionCalls(4u /* expected_count */);
 }
 
 TEST_F(ConnectionManagerTest, AppUrlMigration) {
diff --git a/chrome/browser/chromeos/android_sms/streaming_connection_establisher.cc b/chrome/browser/chromeos/android_sms/streaming_connection_establisher.cc
index 20f08235f18d..2bffdfe58b77 100644
--- a/chrome/browser/chromeos/android_sms/streaming_connection_establisher.cc
+++ b/chrome/browser/chromeos/android_sms/streaming_connection_establisher.cc
@@ -45,7 +45,8 @@ void StreamingConnectionEstablisher::EstablishConnection(
 void StreamingConnectionEstablisher::TearDownConnection(
     const GURL& url,
     content::ServiceWorkerContext* service_worker_context) {
-  service_worker_context->StopAllServiceWorkersForOrigin(url);
+  service_worker_context->StopAllServiceWorkersForOrigin(url.GetOrigin());
+  is_connected_ = false;
 }
 
 void StreamingConnectionEstablisher::SendStartStreamingMessageIfNotConnected(
diff --git a/chrome/browser/chromeos/android_sms/streaming_connection_establisher_unittest.cc b/chrome/browser/chromeos/android_sms/streaming_connection_establisher_unittest.cc
index 13fbd8e71b4a..d19a7f400a6b 100644
--- a/chrome/browser/chromeos/android_sms/streaming_connection_establisher_unittest.cc
+++ b/chrome/browser/chromeos/android_sms/streaming_connection_establisher_unittest.cc
@@ -117,7 +117,19 @@ TEST_F(StreamingConnectionEstablisherTest, TearDownConnection) {
   const auto& stop_calls =
       fake_service_worker_context.stop_all_service_workers_for_origin_calls();
   ASSERT_EQ(1u, stop_calls.size());
-  EXPECT_EQ(GetAndroidMessagesURL(), stop_calls[0]);
+  EXPECT_EQ(GetAndroidMessagesURL().GetOrigin(), stop_calls[0]);
+
+  // Verify that subsequent message message dispatch calls succeed.
+  auto& message_dispatch_calls =
+      fake_service_worker_context
+          .start_service_worker_and_dispatch_long_running_message_calls();
+
+  connection_establisher.EstablishConnection(
+      GetAndroidMessagesURL(),
+      ConnectionEstablisher::ConnectionMode::kStartConnection,
+      &fake_service_worker_context);
+  base::RunLoop().RunUntilIdle();
+  ASSERT_EQ(1u, message_dispatch_calls.size());
 }
 
 }  // namespace android_sms