diff --git a/app/src/main/java/org/thoughtcrime/securesms/messages/NetworkConnectionListener.kt b/app/src/main/java/org/thoughtcrime/securesms/messages/NetworkConnectionListener.kt
index 4d3a58f2ee..c9191cf5fa 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/messages/NetworkConnectionListener.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/messages/NetworkConnectionListener.kt
@@ -44,7 +44,7 @@ class NetworkConnectionListener(private val context: Context, private val onNetw
     networkCapabilities: NetworkCapabilities,
     callbackType: String,
     lastLogs: MutableMap<Network, String>
-  ) {
+  ): Boolean {
     val currentLog = buildString {
       append(callbackType)
       append(" onCapabilitiesChanged($network, ")
@@ -56,7 +56,10 @@ class NetworkConnectionListener(private val context: Context, private val onNetw
     if (lastLogs[network] != currentLog) {
       Log.d(TAG, currentLog)
       lastLogs[network] = currentLog
+      return true
     }
+
+    return false
   }
 
   private val networkChangedCallback: ConnectivityManager.NetworkCallback = object : ConnectivityManager.NetworkCallback() {
@@ -92,7 +95,9 @@ class NetworkConnectionListener(private val context: Context, private val onNetw
 
     override fun onCapabilitiesChanged(network: Network, networkCapabilities: NetworkCapabilities) {
       super.onCapabilitiesChanged(network, networkCapabilities)
-      logCapabilitiesIfChanged(network, networkCapabilities, "ConnectivityManager.NetworkCallback", lastNetworkCapabilities)
+      if (logCapabilitiesIfChanged(network, networkCapabilities, "ConnectivityManager.NetworkCallback", lastNetworkCapabilities)) {
+        onNetworkLost { !networkCapabilities.hasCapability(NetworkCapabilities.NET_CAPABILITY_INTERNET) }
+      }
     }
   }
 
diff --git a/app/src/test/java/org/thoughtcrime/securesms/messages/NetworkConnectionListenerTest.kt b/app/src/test/java/org/thoughtcrime/securesms/messages/NetworkConnectionListenerTest.kt
new file mode 100644
index 0000000000..b44838bd58
--- /dev/null
+++ b/app/src/test/java/org/thoughtcrime/securesms/messages/NetworkConnectionListenerTest.kt
@@ -0,0 +1,59 @@
+package org.thoughtcrime.securesms.messages
+
+import android.app.Application
+import android.net.ConnectivityManager
+import android.net.Network
+import android.net.NetworkCapabilities
+import androidx.test.core.app.ApplicationProvider
+import assertk.assertThat
+import assertk.assertions.containsExactly
+import io.mockk.mockk
+import org.junit.Test
+import org.junit.runner.RunWith
+import org.robolectric.RobolectricTestRunner
+import org.robolectric.annotation.Config
+import org.robolectric.util.ReflectionHelpers
+
+@RunWith(RobolectricTestRunner::class)
+@Config(manifest = Config.NONE, application = Application::class, sdk = [31])
+class NetworkConnectionListenerTest {
+
+  @Test
+  fun `default network capability changes notify listener`() {
+    val unavailableEvents = mutableListOf<Boolean>()
+    val listener = NetworkConnectionListener(
+      context = ApplicationProvider.getApplicationContext(),
+      onNetworkLost = { isNetworkUnavailable -> unavailableEvents += isNetworkUnavailable() },
+      onProxySettingsChanged = {}
+    )
+    val callback = ReflectionHelpers.getField<ConnectivityManager.NetworkCallback>(listener, "networkChangedCallback")
+    val network = mockk<Network>()
+
+    callback.onCapabilitiesChanged(network, capabilities(hasInternet = true, validated = false))
+    callback.onCapabilitiesChanged(network, capabilities(hasInternet = true, validated = false))
+    callback.onCapabilitiesChanged(network, capabilities(hasInternet = true, validated = true))
+    callback.onCapabilitiesChanged(network, capabilities(hasInternet = false, validated = false))
+
+    assertThat(unavailableEvents).containsExactly(false, false, true)
+  }
+
+  private fun capabilities(hasInternet: Boolean, validated: Boolean): NetworkCapabilities {
+    val capabilities = NetworkCapabilities()
+
+    if (hasInternet) {
+      capabilities.addCapabilityReflectively(NetworkCapabilities.NET_CAPABILITY_INTERNET)
+    }
+
+    if (validated) {
+      capabilities.addCapabilityReflectively(NetworkCapabilities.NET_CAPABILITY_VALIDATED)
+    }
+
+    return capabilities
+  }
+
+  private fun NetworkCapabilities.addCapabilityReflectively(capability: Int) {
+    val method = NetworkCapabilities::class.java.getDeclaredMethod("addCapability", Int::class.javaPrimitiveType)
+    method.isAccessible = true
+    method.invoke(this, capability)
+  }
+}
diff --git a/lib/libsignal-service/src/main/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnection.kt b/lib/libsignal-service/src/main/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnection.kt
index 54fdcb6fe5..01099f23e3 100644
--- a/lib/libsignal-service/src/main/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnection.kt
+++ b/lib/libsignal-service/src/main/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnection.kt
@@ -461,7 +461,7 @@ class LibSignalChatConnection(
           },
           onFailure = { throwable ->
             Log.w(TAG, "$name [sendKeepAlive] Failure:", throwable)
-            state.onNext(WebSocketConnectionState.DISCONNECTED)
+            disconnect()
           }
         )
     }
diff --git a/lib/libsignal-service/src/test/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnectionTest.kt b/lib/libsignal-service/src/test/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnectionTest.kt
index d89ce140e1..f786154a30 100644
--- a/lib/libsignal-service/src/test/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnectionTest.kt
+++ b/lib/libsignal-service/src/test/java/org/whispersystems/signalservice/internal/websocket/LibSignalChatConnectionTest.kt
@@ -259,12 +259,13 @@ class LibSignalChatConnectionTest {
   }
 
   // Test keepAlive that fails at the transport layer (send() throws),
-  // which transitions from CONNECTED -> DISCONNECTED.
+  // which disconnects the underlying chat connection before transitioning to DISCONNECTED.
   @Test
   fun keepAliveConnectionFailure() {
     val connectionFailure = RuntimeException("Sending keep-alive failed")
 
     val keepAliveFailureLatch = CountDownLatch(1)
+    disconnectLatch = CountDownLatch(1)
 
     every { chatConnection.send(any()) } answers {
       delay {
@@ -281,15 +282,22 @@ class LibSignalChatConnectionTest {
     connection.sendKeepAlive()
 
     keepAliveFailureLatch.await(100, TimeUnit.MILLISECONDS)
+    disconnectLatch!!.await(100, TimeUnit.MILLISECONDS)
+    observer.awaitCount(3)
 
     observer.assertNotComplete()
     observer.assertValues(
       // We start in the connected state
       WebSocketConnectionState.CONNECTED,
-      // Disconnects as a result of keep-alive failure
+      // Starts an underlying disconnect as a result of keep-alive failure
+      WebSocketConnectionState.DISCONNECTING,
+      // Disconnects once libsignal confirms the connection was interrupted
       WebSocketConnectionState.DISCONNECTED
     )
     observer.assertNoConsecutiveDuplicates()
+    verify(exactly = 1) {
+      chatConnection.disconnect()
+    }
     verify(exactly = 0) {
       healthMonitor.onKeepAliveResponse(any(), any())
       healthMonitor.onMessageError(any(), any())