diff --git a/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsEvents.kt b/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsEvents.kt
new file mode 100644
index 00000000..a98ac589
--- /dev/null
+++ b/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsEvents.kt
@@ -0,0 +1,5 @@
+package eu.darken.capod.main.ui.settings.general
+
+sealed class GeneralSettingsEvents {
+    object SelectDeviceAddressEvent : GeneralSettingsEvents()
+}
diff --git a/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragment.kt b/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragment.kt
index 15fbe7d9..15e74b68 100644
--- a/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragment.kt
+++ b/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragment.kt
@@ -61,6 +61,13 @@ class GeneralSettingsFragment : PreferenceFragment3() {
                 true
             }
         }
+
+        vm.events.observe2 {
+            when (it) {
+                GeneralSettingsEvents.SelectDeviceAddressEvent -> mainDeviceAddressPref.performClick()
+            }
+        }
+
         mainDeviceModelPref.setOnPreferenceClickListener {
             val dialog = ModelSelectionDialogFactory(requireContext()).create(
                 PodDevice.Model.values().toList(),
diff --git a/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragmentVM.kt b/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragmentVM.kt
index f5131f91..907a17e3 100644
--- a/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragmentVM.kt
+++ b/app/src/main/java/eu/darken/capod/main/ui/settings/general/GeneralSettingsFragmentVM.kt
@@ -5,21 +5,41 @@ import dagger.hilt.android.lifecycle.HiltViewModel
 import eu.darken.capod.common.bluetooth.BluetoothManager2
 import eu.darken.capod.common.coroutine.DispatcherProvider
 import eu.darken.capod.common.debug.logging.logTag
+import eu.darken.capod.common.flow.withPrevious
+import eu.darken.capod.common.livedata.SingleLiveEvent
 import eu.darken.capod.common.uix.ViewModel3
+import eu.darken.capod.main.core.GeneralSettings
+import eu.darken.capod.main.core.MonitorMode
+import kotlinx.coroutines.flow.filter
 import kotlinx.coroutines.flow.map
+import kotlinx.coroutines.flow.onEach
 import javax.inject.Inject
 
 @HiltViewModel
 class GeneralSettingsFragmentVM @Inject constructor(
-    private val handle: SavedStateHandle,
-    private val dispatcherProvider: DispatcherProvider,
-    private val bluetoothManager: BluetoothManager2,
+    @Suppress("unused") private val handle: SavedStateHandle,
+    dispatcherProvider: DispatcherProvider,
+    bluetoothManager: BluetoothManager2,
+    private val generalSettings: GeneralSettings,
 ) : ViewModel3(dispatcherProvider) {
 
     val bondedDevices = bluetoothManager.bondedDevices()
         .map { it.toList() }
         .asLiveData2()
 
+    val events = SingleLiveEvent<GeneralSettingsEvents>()
+
+    init {
+
+        generalSettings.monitorMode.flow
+            .withPrevious()
+            .filter { (old, new) ->
+                old != new && new == MonitorMode.AUTOMATIC && generalSettings.mainDeviceAddress.value == null
+            }
+            .onEach { events.postValue(GeneralSettingsEvents.SelectDeviceAddressEvent) }
+            .launchInViewModel()
+    }
+
     companion object {
         private val TAG = logTag("Settings", "General", "VM")
     }
diff --git a/app/src/main/java/eu/darken/capod/monitor/core/worker/MonitorWorker.kt b/app/src/main/java/eu/darken/capod/monitor/core/worker/MonitorWorker.kt
index 12fc8e32..1c46de3f 100644
--- a/app/src/main/java/eu/darken/capod/monitor/core/worker/MonitorWorker.kt
+++ b/app/src/main/java/eu/darken/capod/monitor/core/worker/MonitorWorker.kt
@@ -1,6 +1,7 @@
 package eu.darken.capod.monitor.core.worker
 
 import android.app.NotificationManager
+import android.bluetooth.BluetoothDevice
 import android.content.Context
 import androidx.hilt.work.HiltWorker
 import androidx.work.CoroutineWorker
@@ -114,21 +115,27 @@ class MonitorWorker @AssistedInject constructor(
             }
             .launchIn(workerScope)
 
-        generalSettings.monitorMode.flow
-            .flatMapLatest { monitorMode ->
-                val missingPermsFlow = permissionTool.missingPermissions.first()
+        permissionTool.missingPermissions
+            .flatMapLatest { missingPermsFlow ->
                 if (missingPermsFlow.isNotEmpty()) {
-                    log(TAG, WARN) { "Aborting, permissions are missing for $monitorMode: $missingPermsFlow" }
+                    log(TAG, WARN) { "Aborting, permissions are missing: $missingPermsFlow" }
                     workerScope.coroutineContext.cancelChildren()
                     return@flatMapLatest emptyFlow()
                 }
-
-                bluetoothManager.connectedDevices().map { knownDevices ->
-                    monitorMode to knownDevices
+                combine(
+                    generalSettings.monitorMode.flow,
+                    generalSettings.mainDeviceAddress.flow,
+                    bluetoothManager.connectedDevices(),
+                ) { monitorMode, mainAddress, connectedDevices ->
+                    listOf(monitorMode, mainAddress, connectedDevices)
                 }
             }
             .setupCommonEventHandlers(TAG) { "MonitorMode" }
-            .flatMapLatest { (monitorMode, devices) ->
+            .flatMapLatest { arguments ->
+                val monitorMode = arguments[0] as MonitorMode
+                val mainAddress = arguments[1] as String?
+                val devices = arguments[2] as Collection<BluetoothDevice>
+
                 log(TAG) { "Monitor mode: $monitorMode" }
                 when (monitorMode) {
                     MonitorMode.MANUAL -> flow<Unit> {
@@ -137,15 +144,20 @@ class MonitorWorker @AssistedInject constructor(
                     }
                     MonitorMode.ALWAYS -> emptyFlow()
                     MonitorMode.AUTOMATIC -> flow {
-                        val mainAddress = generalSettings.mainDeviceAddress.value
-                        if (devices.any { it.address == mainAddress }) {
-                            log(TAG) { "MainDevice is connected ($mainAddress), aborting any timeout." }
-                        } else {
-                            log(TAG) { "No Pods are connected, canceling worker soon." }
-                            delay(15 * 1000)
-                            log(TAG) { "Canceling worker now, still no Pods connected." }
+                        when {
+                            mainAddress == null && devices.isNotEmpty() -> {
+                                log(TAG, WARN) { "Main device address not set, staying alive while any is connected" }
+                            }
+                            devices.any { it.address == mainAddress } -> {
+                                log(TAG) { "MainDevice is connected ($mainAddress), aborting any timeout." }
+                            }
+                            else -> {
+                                log(TAG) { "No known Pods are connected, canceling worker soon." }
+                                delay(15 * 1000)
+                                log(TAG) { "Canceling worker now, still no Pods connected." }
 
-                            workerScope.coroutineContext.cancelChildren()
+                                workerScope.coroutineContext.cancelChildren()
+                            }
                         }
                     }
                 }