diff --git a/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkController.java b/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkController.java
index c87ced5e..a7f6216c 100644
--- a/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkController.java
+++ b/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkController.java
@@ -10,6 +10,7 @@
 import android.os.RemoteException;
 import android.util.Log;
 
+import java9.util.concurrent.CompletableFuture;
 import java.util.concurrent.atomic.AtomicBoolean;
 
 /**
@@ -23,10 +24,12 @@ public class WorkController {
     private final Context context;
     private Connection connection;
     private Messenger messenger;
+    private CompletableFuture<Messenger> connected;
     private final AtomicBoolean isConnected = new AtomicBoolean(false);
 
     private WorkController(Context context) {
         this.context = context;
+        this.connected = new CompletableFuture<>();
     }
 
     public static WorkController getInstance(Context context) {
@@ -109,6 +112,9 @@ protected void dispatch(Message message, int attempts) {
         synchronized (isConnected) {
             // If we're already connected, then it's awake
             if (!isConnected.get()) {
+                if (connected.isDone()) {
+                    connected = new CompletableFuture<>();
+                }
                 // Binding allows us to monitor the connection state
                 context.bindService(
                         new Intent(context, WorkControllerService.class),
@@ -118,21 +124,23 @@ protected void dispatch(Message message, int attempts) {
             }
         }
 
-        // Start the service with this intent
-        try {
-            messenger.send(message);
-        } catch (RemoteException e) {
-            // If the remote process has died, then we need to rebind
-            synchronized (isConnected) {
-                isConnected.set(false);
-                messenger = null;
-            }
-            if (attempts < 3) {
-                dispatch(message, attempts + 1);
+        connected.thenApply((messenger) -> {
+            try {
+                messenger.send(message);
+            } catch (RemoteException e) {
+                // If the remote process has died, then we need to rebind
+                synchronized (isConnected) {
+                    isConnected.set(false);
+                    messenger = null;
+                }
+                if (attempts < 3) {
+                    dispatch(message, attempts + 1);
+                }
+            } catch (Exception e) {
+                Log.e(TAG, "Failed to send message " + message, e);
             }
-        } catch (Exception e) {
-            Log.e(TAG, "Failed to send message " + message, e);
-        }
+            return messenger;
+        });
     }
 
     public class Connection implements ServiceConnection {
@@ -141,6 +149,7 @@ public void onServiceConnected(ComponentName name, IBinder service) {
             synchronized (isConnected) {
                 isConnected.set(true);
                 messenger = new Messenger(service);
+                connected.complete(messenger);
             }
         }
 
diff --git a/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkControllerService.java b/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkControllerService.java
index c2e9618a..2c0d755d 100644
--- a/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkControllerService.java
+++ b/python-for-android/dists/kolibri/src/main/java/org/learningequality/Kolibri/WorkControllerService.java
@@ -28,7 +28,7 @@
  * initializing the work manager in the task worker process.
  */
 public class WorkControllerService extends Service {
-    public static final String TAG = "Kolibri.MonitorService";
+    public static final String TAG = "Kolibri.WorkControllerService";
     public static final int ACTION_WAKE = 1;
     public static final int ACTION_SLEEP = 2;
     public static final int ACTION_STOP = 3;
@@ -75,6 +75,7 @@ public void onDestroy() {
     }
 
     protected void onWake() {
+        Log.d(TAG, "Waking up work controller service");
         synchronized (state) {
             if (state.get() != State.AWAKE_LOW_MEMORY) {
                 state.set(State.AWAKE);
@@ -89,6 +90,7 @@ protected void onWake() {
         }
 
         startTask(() -> {
+            Log.d(TAG, "Binding to work manager service");
             // Wakey wakey remote work manager service
             bindService(workManagerIntent, connection, Context.BIND_AUTO_CREATE);
             return null;
@@ -96,18 +98,23 @@ protected void onWake() {
     }
 
     protected void onReconcile() {
-        startTask(() -> Task.reconcile(getApplicationContext(), executor)
-                .thenApply((r) -> {
-                    if (r) {
-                        Log.d(TAG, "Reconciliation task completed");
-                    } else {
-                        Log.d(TAG, "Reconciliation task failed");
-                    }
-                    return null;
-                }));
+        Log.d(TAG, "Enqueuing task reconciliation");
+        startTask(() -> {
+            Log.d(TAG, "Running task reconciliation");
+            return Task.reconcile(getApplicationContext(), executor)
+                    .thenApply((r) -> {
+                        if (r) {
+                            Log.d(TAG, "Reconciliation task completed");
+                        } else {
+                            Log.d(TAG, "Reconciliation task failed");
+                        }
+                        return null;
+                    });
+        });
     }
 
     protected void onSleep() {
+        Log.d(TAG, "Sleeping work controller service");
         synchronized (state) {
             state.set(State.SLEEPING);
         }
@@ -115,11 +122,14 @@ protected void onSleep() {
             if (taskCount.get() == 0) {
                 Log.d(TAG, "Stopping service due to no more tasks");
                 stopSelf();
+            } else {
+                Log.d(TAG, "Waiting for " + taskCount.get() + " tasks to complete");
             }
         }
     }
 
     protected void onStop() {
+        Log.d(TAG, "Stopping work controller service");
         // should eventually call `onDestroy` and that will set the stopped state
         stopSelf();
     }
@@ -127,6 +137,7 @@ protected void onStop() {
     protected void startTask(WorkTask task) {
         futureChain = futureChain.thenComposeAsync((nothing) -> {
             try {
+                Log.d(TAG, "Running task");
                 CompletableFuture<Void> f = task.run();
                 if (f != null) {
                     return f;
@@ -134,8 +145,10 @@ protected void startTask(WorkTask task) {
             } catch (Exception e) {
                 Log.e(TAG, "Failed running task", e);
             } finally {
+                Log.d(TAG, "Task completed");
                 synchronized (taskCount) {
                     if (taskCount.decrementAndGet() == 0) {
+                        Log.d(TAG, "Checking state for stopping service");
                         synchronized (state) {
                             if (state.get() != State.AWAKE) {
                                 Log.d(TAG, "Stopping service due to no more tasks");