diff --git a/app/src/main/java/xyz/cottongin/radio247/service/RadioPlaybackService.kt b/app/src/main/java/xyz/cottongin/radio247/service/RadioPlaybackService.kt
index 1680d44..55d076a 100644
--- a/app/src/main/java/xyz/cottongin/radio247/service/RadioPlaybackService.kt
+++ b/app/src/main/java/xyz/cottongin/radio247/service/RadioPlaybackService.kt
@@ -1,6 +1,7 @@
 package xyz.cottongin.radio247.service
 
 import android.app.PendingIntent
+import android.app.Service
 import android.content.Context
 import android.content.Intent
 import android.net.ConnectivityManager
@@ -38,6 +39,8 @@ import kotlin.coroutines.coroutineContext
 import kotlinx.coroutines.CompletableDeferred
 import kotlinx.coroutines.Job
 
+class ConnectionFailedException(cause: Throwable) : Exception("Connection failed", cause)
+
 class RadioPlaybackService : LifecycleService() {
     companion object {
         const val ACTION_PLAY = "xyz.cottongin.radio247.PLAY"
@@ -91,6 +94,10 @@ class RadioPlaybackService : LifecycleService() {
 
     private var playJob: Job? = null
 
+    private fun transition(newState: PlaybackState) {
+        controller.updateState(newState)
+    }
+
     override fun onCreate() {
         super.onCreate()
         notificationHelper.createChannel()
@@ -131,7 +138,7 @@ class RadioPlaybackService : LifecycleService() {
             if (station != null) {
                 handlePlay(station, reuseSession = isResume)
             } else {
-                controller.updateState(PlaybackState.Idle)
+                transition(PlaybackState.Idle)
                 stopSelf()
             }
         }
@@ -171,7 +178,8 @@ class RadioPlaybackService : LifecycleService() {
         startForegroundWithPlaceholder(station)
 
         try {
-            startEngine(station)
+            val urls = app.streamResolver.resolveUrls(station)
+            startEngine(station, urls)
             if (stayConnected) {
                 reconnectLoop(station)
             }
@@ -181,22 +189,21 @@ class RadioPlaybackService : LifecycleService() {
             }
         } finally {
             endConnectionSpan()
-            when (controller.state.value) {
-                is PlaybackState.Paused -> {
+            val currentState = controller.state.value
+            when {
+                currentState is PlaybackState.Paused -> {
                     updateNotification(station, currentMetadata, isReconnecting = false, isPaused = true)
                 }
-                is PlaybackState.Idle -> {
-                    endListeningSession()
+                else -> {
                     val isActiveJob = playJob == coroutineContext[Job]
                     if (isActiveJob) {
+                        transition(PlaybackState.Idle)
+                        endListeningSession()
                         cleanupResources()
-                        stopForeground(STOP_FOREGROUND_REMOVE)
+                        stopForeground(Service.STOP_FOREGROUND_REMOVE)
                         stopSelf()
                     }
                 }
-                else -> {
-                    // Connecting to a new station or other transition -- another job takes over
-                }
             }
         }
     }
@@ -256,81 +263,104 @@ class RadioPlaybackService : LifecycleService() {
         }
     }
 
-    private suspend fun startEngine(station: Station) {
+    private suspend fun startEngine(station: Station, urls: List<String>) {
+        for ((index, url) in urls.withIndex()) {
+            reconnectionMutex.withLock {
+                engine?.stop()
+                transition(
+                    PlaybackState.Connecting(
+                        station = station,
+                        urls = urls,
+                        currentUrlIndex = index,
+                        sessionStartedAt = sessionStartedAt
+                    )
+                )
+                updateNotification(station, null, isReconnecting = false)
+
+                val bufferMs = app.preferences.bufferMs.first()
+                engine = AudioEngine(url, bufferMs)
+                connectionSpanId = connectionSpanDao.insert(
+                    ConnectionSpan(
+                        sessionId = listeningSessionId,
+                        startedAt = System.currentTimeMillis()
+                    )
+                )
+                currentMetadata = null
+                engine!!.start()
+            }
+
+            try {
+                awaitEngine(station)
+                return
+            } catch (e: Exception) {
+                endConnectionSpan()
+                if (e is ConnectionFailedException && index < urls.size - 1) {
+                    continue
+                }
+                throw e
+            }
+        }
+        throw Exception("All URLs exhausted")
+    }
+
+    private suspend fun awaitEngine(station: Station) {
         val deferred = CompletableDeferred<Unit>()
-        reconnectionMutex.withLock {
-            engine?.stop()
-            val bufferMs = app.preferences.bufferMs.first()
-            val urls = app.streamResolver.resolveUrls(station)
-            engine = AudioEngine(urls.first(), bufferMs)
-            connectionSpanId = connectionSpanDao.insert(
-                ConnectionSpan(
-                    sessionId = listeningSessionId,
-                    startedAt = System.currentTimeMillis()
-                )
-            )
-            currentMetadata = null
-            val connectionStartedAt = System.currentTimeMillis()
+        val connectionStartedAt = System.currentTimeMillis()
 
-            controller.updateState(
-                PlaybackState.Playing(
-                    station = station,
-                    metadata = null,
-                    sessionStartedAt = sessionStartedAt,
-                    connectionStartedAt = connectionStartedAt
-                )
-            )
-            updateNotification(station, null, false)
-
-            engine!!.start()
-
-            serviceScope.launch collector@ {
-                engine!!.events.collect { event ->
-                    when (event) {
-                        is AudioEngineEvent.MetadataChanged -> {
-                            currentMetadata = event.metadata
-                            val playingState = controller.state.value
-                            if (playingState is PlaybackState.Playing) {
-                                controller.updateState(
-                                    playingState.copy(metadata = event.metadata)
-                                )
-                            }
-                            updateNotification(station, event.metadata, false)
-                            persistMetadataSnapshot(station.id, event.metadata)
+        serviceScope.launch {
+            engine!!.events.collect { event ->
+                when (event) {
+                    is AudioEngineEvent.Started -> {
+                        transition(
+                            PlaybackState.Playing(
+                                station = station,
+                                metadata = null,
+                                sessionStartedAt = sessionStartedAt,
+                                connectionStartedAt = connectionStartedAt
+                            )
+                        )
+                        updateNotification(station, null, false)
+                        controller.updateLatency(engine!!.estimatedLatencyMs)
+                    }
+                    is AudioEngineEvent.MetadataChanged -> {
+                        currentMetadata = event.metadata
+                        val playingState = controller.state.value
+                        if (playingState is PlaybackState.Playing) {
+                            transition(playingState.copy(metadata = event.metadata))
                         }
-                        is AudioEngineEvent.StreamInfoReceived -> {
-                            val playingState = controller.state.value
-                            if (playingState is PlaybackState.Playing) {
-                                controller.updateState(
-                                    playingState.copy(streamInfo = event.streamInfo)
-                                )
-                            }
-                        }
-                        is AudioEngineEvent.Started -> {
-                            controller.updateLatency(engine!!.estimatedLatencyMs)
-                        }
-                        is AudioEngineEvent.Error -> {
-                            endConnectionSpan()
-                            engine?.stop()
-                            engine = null
-                            val throwable = when (val cause = event.cause) {
-                                is EngineError.ConnectionFailed -> cause.cause
-                                is EngineError.StreamEnded -> Exception("Stream ended")
-                                is EngineError.DecoderError -> cause.cause
-                                is EngineError.AudioOutputError -> cause.cause
-                            }
-                            deferred.completeExceptionally(throwable)
-                            return@collect
-                        }
-                        is AudioEngineEvent.Stopped -> {
-                            deferred.complete(Unit)
-                            return@collect
+                        updateNotification(station, event.metadata, false)
+                        persistMetadataSnapshot(station.id, event.metadata)
+                    }
+                    is AudioEngineEvent.StreamInfoReceived -> {
+                        val playingState = controller.state.value
+                        if (playingState is PlaybackState.Playing) {
+                            transition(playingState.copy(streamInfo = event.streamInfo))
                         }
                     }
+                    is AudioEngineEvent.Error -> {
+                        engine?.stop()
+                        engine = null
+                        val throwable = when (val cause = event.cause) {
+                            is EngineError.ConnectionFailed ->
+                                ConnectionFailedException(cause.cause)
+                            is EngineError.StreamEnded ->
+                                Exception("Stream ended")
+                            is EngineError.DecoderError ->
+                                cause.cause
+                            is EngineError.AudioOutputError ->
+                                cause.cause
+                        }
+                        deferred.completeExceptionally(throwable)
+                        return@collect
+                    }
+                    is AudioEngineEvent.Stopped -> {
+                        deferred.complete(Unit)
+                        return@collect
+                    }
                 }
-                if (!deferred.isCompleted) {
-                    deferred.completeExceptionally(Exception("Event flow completed unexpectedly"))
-                }
+            }
+            if (!deferred.isCompleted) {
+                deferred.completeExceptionally(Exception("Event flow completed unexpectedly"))
             }
         }
         deferred.await()
@@ -344,7 +374,7 @@ class RadioPlaybackService : LifecycleService() {
                 retryImmediatelyOnNetwork = false
             } else {
                 attempt++
-                controller.updateState(
+                transition(
                     PlaybackState.Reconnecting(
                         station = station,
                         metadata = currentMetadata,
@@ -363,7 +393,8 @@ class RadioPlaybackService : LifecycleService() {
             }
             if (!stayConnected) break
             try {
-                startEngine(station)
+                val urls = app.streamResolver.resolveUrls(station)
+                startEngine(station, urls)
                 return
             } catch (_: Exception) {
                 // Continue loop