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 34d58ae707..4d3a58f2ee 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/messages/NetworkConnectionListener.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/messages/NetworkConnectionListener.kt
@@ -12,6 +12,8 @@ import android.content.IntentFilter
 import android.net.ConnectivityManager
 import android.net.LinkProperties
 import android.net.Network
+import android.net.NetworkCapabilities
+import android.net.NetworkRequest
 import android.net.ProxyInfo
 import android.os.Build
 import org.signal.core.util.logging.Log
@@ -32,6 +34,30 @@ class NetworkConnectionListener(private val context: Context, private val onNetw
   }
 
   private val connectivityManager = ServiceUtil.getConnectivityManager(context)
+  private val lastNetworkCapabilities = mutableMapOf<Network, String>()
+  private val lastValidatedNetworkCapabilities = mutableMapOf<Network, String>()
+
+  // onCapabilitiesChanged gets called every ~30 seconds or so in my testing, as the network estimator runs
+  // and updates the bandwidth estimated capabilities. This is thus essential for preventing log spam.
+  private fun logCapabilitiesIfChanged(
+    network: Network,
+    networkCapabilities: NetworkCapabilities,
+    callbackType: String,
+    lastLogs: MutableMap<Network, String>
+  ) {
+    val currentLog = buildString {
+      append(callbackType)
+      append(" onCapabilitiesChanged($network, ")
+      append("hasInternet=${networkCapabilities.hasCapability(NetworkCapabilities.NET_CAPABILITY_INTERNET)}, ")
+      append("validated=${networkCapabilities.hasCapability(NetworkCapabilities.NET_CAPABILITY_VALIDATED)}, ")
+      append("captivePortal=${networkCapabilities.hasCapability(NetworkCapabilities.NET_CAPABILITY_CAPTIVE_PORTAL)})")
+    }
+
+    if (lastLogs[network] != currentLog) {
+      Log.d(TAG, currentLog)
+      lastLogs[network] = currentLog
+    }
+  }
 
   private val networkChangedCallback: ConnectivityManager.NetworkCallback = object : ConnectivityManager.NetworkCallback() {
     override fun onUnavailable() {
@@ -63,6 +89,11 @@ class NetworkConnectionListener(private val context: Context, private val onNetw
       Log.d(TAG, "ConnectivityManager.NetworkCallback onLinkPropertiesChanged($network)")
       onProxySettingsChanged(linkProperties.httpProxy)
     }
+
+    override fun onCapabilitiesChanged(network: Network, networkCapabilities: NetworkCapabilities) {
+      super.onCapabilitiesChanged(network, networkCapabilities)
+      logCapabilitiesIfChanged(network, networkCapabilities, "ConnectivityManager.NetworkCallback", lastNetworkCapabilities)
+    }
   }
 
   private val connectionReceiver = object : BroadcastReceiver() {
@@ -72,9 +103,41 @@ class NetworkConnectionListener(private val context: Context, private val onNetw
     }
   }
 
+  private val logOnlyValidatedNetworkCallback: ConnectivityManager.NetworkCallback = object : ConnectivityManager.NetworkCallback() {
+    override fun onUnavailable() {
+      Log.d(TAG, "ValidatedNetworkCallback onUnavailable()")
+      super.onUnavailable()
+    }
+
+    override fun onAvailable(network: Network) {
+      super.onAvailable(network)
+      Log.d(TAG, "ValidatedNetworkCallback onAvailable($network)")
+    }
+
+    override fun onLost(network: Network) {
+      super.onLost(network)
+      Log.d(TAG, "ValidatedNetworkCallback onLost($network)")
+    }
+
+    override fun onBlockedStatusChanged(network: Network, blocked: Boolean) {
+      super.onBlockedStatusChanged(network, blocked)
+      Log.d(TAG, "ValidatedNetworkCallback onBlockedStatusChanged($network, $blocked)")
+    }
+
+    // This should not be strictly necessary, but seeing as what we're doing here is trying to get more
+    // insight into cases where Android's ConnectivityManager is behaving unexpectedly, I tend towards
+    // logging more rather than less.
+    override fun onCapabilitiesChanged(network: Network, networkCapabilities: NetworkCapabilities) {
+      super.onCapabilitiesChanged(network, networkCapabilities)
+      logCapabilitiesIfChanged(network, networkCapabilities, "ValidatedNetworkCallback", lastValidatedNetworkCapabilities)
+    }
+  }
+
   fun register() {
     if (Build.VERSION.SDK_INT >= 28) {
       connectivityManager.registerDefaultNetworkCallback(networkChangedCallback)
+      val validatedNetworkRequest = NetworkRequest.Builder().addCapability(NetworkCapabilities.NET_CAPABILITY_VALIDATED).build()
+      connectivityManager.registerNetworkCallback(validatedNetworkRequest, logOnlyValidatedNetworkCallback)
     } else {
       context.registerReceiver(connectionReceiver, IntentFilter(ConnectivityManager.CONNECTIVITY_ACTION))
     }
@@ -83,6 +146,7 @@ class NetworkConnectionListener(private val context: Context, private val onNetw
   fun unregister() {
     if (Build.VERSION.SDK_INT >= 28) {
       connectivityManager.unregisterNetworkCallback(networkChangedCallback)
+      connectivityManager.unregisterNetworkCallback(logOnlyValidatedNetworkCallback)
     } else {
       context.unregisterReceiver(connectionReceiver)
     }