diff --git a/core/src/main/java/hu/bbara/purefin/core/data/NetworkMonitor.kt b/core/src/main/java/hu/bbara/purefin/core/data/NetworkMonitor.kt
index ffa3e9a2..97aa8b53 100644
--- a/core/src/main/java/hu/bbara/purefin/core/data/NetworkMonitor.kt
+++ b/core/src/main/java/hu/bbara/purefin/core/data/NetworkMonitor.kt
@@ -4,4 +4,8 @@ import kotlinx.coroutines.flow.Flow
 
 interface NetworkMonitor {
     val isOnline: Flow<Boolean>
+
+    fun reportRequestSucceeded()
+
+    fun reportRequestFailed(error: Throwable)
 }
diff --git a/data/src/main/java/hu/bbara/purefin/data/jellyfin/ConnectivityNetworkMonitor.kt b/data/src/main/java/hu/bbara/purefin/data/jellyfin/ConnectivityNetworkMonitor.kt
index 5a954123..a4246676 100644
--- a/data/src/main/java/hu/bbara/purefin/data/jellyfin/ConnectivityNetworkMonitor.kt
+++ b/data/src/main/java/hu/bbara/purefin/data/jellyfin/ConnectivityNetworkMonitor.kt
@@ -7,28 +7,54 @@ import android.net.NetworkCapabilities
 import android.net.NetworkRequest
 import dagger.hilt.android.qualifiers.ApplicationContext
 import hu.bbara.purefin.core.data.NetworkMonitor
+import kotlinx.coroutines.CoroutineScope
+import kotlinx.coroutines.Dispatchers
+import kotlinx.coroutines.SupervisorJob
 import kotlinx.coroutines.channels.awaitClose
 import kotlinx.coroutines.flow.Flow
+import kotlinx.coroutines.flow.MutableStateFlow
+import kotlinx.coroutines.flow.SharingStarted
+import kotlinx.coroutines.flow.StateFlow
 import kotlinx.coroutines.flow.callbackFlow
+import kotlinx.coroutines.flow.combine
 import kotlinx.coroutines.flow.distinctUntilChanged
+import kotlinx.coroutines.flow.stateIn
+import java.net.ConnectException
+import java.net.NoRouteToHostException
+import java.net.SocketTimeoutException
+import java.net.UnknownHostException
 import javax.inject.Inject
 import javax.inject.Singleton
 
 @Singleton
 class ConnectivityNetworkMonitor @Inject constructor(
-    @ApplicationContext private val context: Context,
+    @param:ApplicationContext private val context: Context,
 ) : NetworkMonitor {
 
-    override val isOnline: Flow<Boolean> = callbackFlow {
-        val connectivityManager = context.getSystemService(ConnectivityManager::class.java)
+    private val scope = CoroutineScope(SupervisorJob() + Dispatchers.IO)
+    private val connectivityManager = context.getSystemService(ConnectivityManager::class.java)
+    private val isServerReachable = MutableStateFlow(true)
+
+    private val isDeviceOnline: Flow<Boolean> = callbackFlow {
+        var wasDeviceOnline = connectivityManager.isCurrentlyConnected()
 
         val callback = object : ConnectivityManager.NetworkCallback() {
-            override fun onAvailable(network: Network) {
-                trySend(true)
+            override fun onCapabilitiesChanged(
+                network: Network,
+                networkCapabilities: NetworkCapabilities
+            ) {
+                val isCurrentlyConnected = connectivityManager.isCurrentlyConnected()
+                if (isCurrentlyConnected && !wasDeviceOnline) {
+                    isServerReachable.value = true
+                }
+                wasDeviceOnline = isCurrentlyConnected
+                trySend(isCurrentlyConnected)
             }
 
             override fun onLost(network: Network) {
-                trySend(connectivityManager.isCurrentlyConnected())
+                val isCurrentlyConnected = connectivityManager.isCurrentlyConnected()
+                wasDeviceOnline = isCurrentlyConnected
+                trySend(isCurrentlyConnected)
             }
         }
 
@@ -36,14 +62,51 @@ class ConnectivityNetworkMonitor @Inject constructor(
             .addCapability(NetworkCapabilities.NET_CAPABILITY_INTERNET)
             .build()
 
-        trySend(connectivityManager.isCurrentlyConnected())
+        trySend(wasDeviceOnline)
         connectivityManager.registerNetworkCallback(request, callback)
         awaitClose { connectivityManager.unregisterNetworkCallback(callback) }
     }.distinctUntilChanged()
 
+    override val isOnline: StateFlow<Boolean> = combine(
+        isDeviceOnline,
+        isServerReachable
+    ) { isDeviceOnline, isServerReachable ->
+        isDeviceOnline && isServerReachable
+    }.distinctUntilChanged()
+        .stateIn(
+            scope = scope,
+            started = SharingStarted.Eagerly,
+            initialValue = connectivityManager.isCurrentlyConnected() && isServerReachable.value
+        )
+
+    override fun reportRequestSucceeded() {
+        isServerReachable.value = true
+    }
+
+    override fun reportRequestFailed(error: Throwable) {
+        if (error.isConnectivityFailure()) {
+            isServerReachable.value = false
+        }
+    }
+
     private fun ConnectivityManager.isCurrentlyConnected(): Boolean {
         val network = activeNetwork ?: return false
         val caps = getNetworkCapabilities(network) ?: return false
-        return caps.hasCapability(NetworkCapabilities.NET_CAPABILITY_INTERNET)
+        return caps.hasCapability(NetworkCapabilities.NET_CAPABILITY_INTERNET) &&
+            caps.hasCapability(NetworkCapabilities.NET_CAPABILITY_VALIDATED)
+    }
+
+    private fun Throwable.isConnectivityFailure(): Boolean {
+        var current: Throwable? = this
+        while (current != null) {
+            when (current) {
+                is UnknownHostException,
+                is ConnectException,
+                is NoRouteToHostException,
+                is SocketTimeoutException -> return true
+            }
+            current = current.cause
+        }
+        return false
     }
 }
diff --git a/data/src/main/java/hu/bbara/purefin/data/jellyfin/client/JellyfinApiClient.kt b/data/src/main/java/hu/bbara/purefin/data/jellyfin/client/JellyfinApiClient.kt
index 5fc68a43..83a6a819 100644
--- a/data/src/main/java/hu/bbara/purefin/data/jellyfin/client/JellyfinApiClient.kt
+++ b/data/src/main/java/hu/bbara/purefin/data/jellyfin/client/JellyfinApiClient.kt
@@ -4,6 +4,7 @@ import android.content.Context
 import android.os.SystemClock
 import dagger.hilt.android.qualifiers.ApplicationContext
 import hu.bbara.purefin.core.data.JellyfinServerCandidate
+import hu.bbara.purefin.core.data.NetworkMonitor
 import hu.bbara.purefin.core.data.PlaybackMethod
 import hu.bbara.purefin.core.data.PlaybackReportContext
 import hu.bbara.purefin.core.data.QuickConnectSession
@@ -64,8 +65,9 @@ import javax.inject.Singleton
 
 @Singleton
 class JellyfinApiClient @Inject constructor(
-    @ApplicationContext private val applicationContext: Context,
+    @param:ApplicationContext private val applicationContext: Context,
     private val userSessionRepository: UserSessionRepository,
+    private val networkMonitor: NetworkMonitor,
 ) {
     private val jellyfin = createJellyfin {
         context = applicationContext
@@ -583,12 +585,14 @@ class JellyfinApiClient @Inject constructor(
         val startedAt = SystemClock.elapsedRealtime()
         return try {
             val result = block()
+            networkMonitor.reportRequestSucceeded()
             val elapsedMs = SystemClock.elapsedRealtime() - startedAt
             Timber.tag(TAG).d("$functionName took ${elapsedMs}ms")
             result
         } catch (error: CancellationException) {
             throw error
         } catch (error: Exception) {
+            networkMonitor.reportRequestFailed(error)
             val elapsedMs = SystemClock.elapsedRealtime() - startedAt
             Timber.tag(TAG).e(error, "$functionName failed after ${elapsedMs}ms")
             throw error