diff --git a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ChangesHappened.java b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ChangesHappened.java
index e0c969862..5ee232094 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ChangesHappened.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ChangesHappened.java
@@ -140,7 +140,11 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
                     if (serverColumn == null)
                         throw new RuntimeException("No server column found for local column " + localColumn + " in table " + table);
 
-                    changeJson.put("value", localProperty.accept(visitor, change));
+                    Object value = localProperty.accept(visitor, change);
+                    if (!validateValue(localProperty, value))
+                        return null;
+
+                    changeJson.put("value", value);
                 }
 
                 changeJson.put("column", serverColumn);
@@ -176,6 +180,16 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
         }
     }
 
+    // Return false if value is detected to be something that would definitely cause a server error
+    // (e.g. empty task title, etc.)
+    private boolean validateValue(Property<?> property, Object value) {
+        if (Task.TITLE.equals(property)) {
+            if (!(value instanceof String) || TextUtils.isEmpty((String) value))
+                return false;
+        }
+        return true;
+    }
+
     private JSONObject getFileJson(String value) {
         try {
             JSONObject obj = new JSONObject(value);
diff --git a/astrid/src/com/todoroo/astrid/service/TaskService.java b/astrid/src/com/todoroo/astrid/service/TaskService.java
index d2a996671..f217e93e6 100644
--- a/astrid/src/com/todoroo/astrid/service/TaskService.java
+++ b/astrid/src/com/todoroo/astrid/service/TaskService.java
@@ -35,12 +35,14 @@ import com.todoroo.astrid.dao.MetadataDao;
 import com.todoroo.astrid.dao.MetadataDao.MetadataCriteria;
 import com.todoroo.astrid.dao.TaskDao;
 import com.todoroo.astrid.dao.TaskDao.TaskCriteria;
+import com.todoroo.astrid.dao.TaskOutstandingDao;
 import com.todoroo.astrid.dao.UserActivityDao;
 import com.todoroo.astrid.data.History;
 import com.todoroo.astrid.data.Metadata;
 import com.todoroo.astrid.data.RemoteModel;
 import com.todoroo.astrid.data.SyncFlags;
 import com.todoroo.astrid.data.Task;
+import com.todoroo.astrid.data.TaskOutstanding;
 import com.todoroo.astrid.data.User;
 import com.todoroo.astrid.data.UserActivity;
 import com.todoroo.astrid.gcal.GCalHelper;
@@ -78,6 +80,9 @@ public class TaskService {
     @Autowired
     private TaskDao taskDao;
 
+    @Autowired
+    private TaskOutstandingDao taskOutstandingDao;
+
     @Autowired
     private MetadataDao metadataDao;
 
@@ -242,6 +247,7 @@ public class TaskService {
             return;
         else if(item.containsValue(Task.TITLE) && item.getValue(Task.TITLE).length() == 0) {
             taskDao.delete(item.getId());
+            taskOutstandingDao.deleteWhere(TaskOutstanding.ENTITY_ID_PROPERTY.eq(item.getId()));
             item.setId(Task.NO_ID);
         } else {
             long id = item.getId();