diff --git a/api/src/com/todoroo/astrid/data/TaskAttachment.java b/api/src/com/todoroo/astrid/data/TaskAttachment.java
index c3ea0fb9c..26f7b0bdb 100644
--- a/api/src/com/todoroo/astrid/data/TaskAttachment.java
+++ b/api/src/com/todoroo/astrid/data/TaskAttachment.java
@@ -16,6 +16,7 @@ import com.todoroo.andlib.data.Property.LongProperty;
 import com.todoroo.andlib.data.Property.StringProperty;
 import com.todoroo.andlib.data.Table;
 import com.todoroo.andlib.data.TodorooCursor;
+import com.todoroo.andlib.utility.DateUtilities;
 import com.todoroo.astrid.api.AstridApiConstants;
 
 /**
@@ -32,6 +33,9 @@ public final class TaskAttachment extends RemoteModel {
     /** table for this model */
     public static final Table TABLE = new Table("task_attachments", TaskAttachment.class);
 
+    /** model class for entries in the outstanding table */
+    public static final Class<? extends OutstandingEntry<TaskAttachment>> OUTSTANDING_MODEL = TaskAttachmentOutstanding.class;
+
     /** content uri for this model */
     public static final Uri CONTENT_URI = Uri.parse("content://" + AstridApiConstants.API_PACKAGE + "/" +
             TABLE.name);
@@ -147,6 +151,7 @@ public final class TaskAttachment extends RemoteModel {
         attachment.setValue(USER_UUID, Task.USER_ID_SELF);
         attachment.setValue(FILE_PATH, filePath);
         attachment.setValue(CONTENT_TYPE, fileType);
+        attachment.setValue(CREATED_AT, DateUtilities.now());
         attachment.setValue(DELETED_AT, 0L);
         return attachment;
     }
diff --git a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmSyncThread.java b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmSyncThread.java
index 7c4526bf2..413d43c45 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmSyncThread.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmSyncThread.java
@@ -32,6 +32,7 @@ import com.todoroo.astrid.dao.OutstandingEntryDao;
 import com.todoroo.astrid.dao.RemoteModelDao;
 import com.todoroo.astrid.dao.TagDataDao;
 import com.todoroo.astrid.dao.TagOutstandingDao;
+import com.todoroo.astrid.dao.TaskAttachmentDao;
 import com.todoroo.astrid.dao.TaskDao;
 import com.todoroo.astrid.dao.TaskOutstandingDao;
 import com.todoroo.astrid.dao.UserActivityDao;
@@ -41,6 +42,7 @@ import com.todoroo.astrid.data.RemoteModel;
 import com.todoroo.astrid.data.TagData;
 import com.todoroo.astrid.data.TagOutstanding;
 import com.todoroo.astrid.data.Task;
+import com.todoroo.astrid.data.TaskAttachment;
 import com.todoroo.astrid.data.TaskOutstanding;
 import com.todoroo.astrid.data.User;
 import com.todoroo.astrid.data.UserActivity;
@@ -87,7 +89,8 @@ public class ActFmSyncThread {
     public static enum ModelType {
         TYPE_TASK,
         TYPE_TAG,
-        TYPE_ACTIVITY
+        TYPE_ACTIVITY,
+        TYPE_ATTACHMENT
     }
 
     private static volatile ActFmSyncThread instance;
@@ -96,14 +99,14 @@ public class ActFmSyncThread {
         if (instance == null) {
             synchronized(ActFmSyncThread.class) {
                 if (instance == null) {
-                    initializeSyncComponents(PluginServices.getTaskDao(), PluginServices.getTagDataDao(), PluginServices.getUserActivityDao());
+                    initializeSyncComponents(PluginServices.getTaskDao(), PluginServices.getTagDataDao(), PluginServices.getUserActivityDao(), PluginServices.getTaskAttachmentDao());
                 }
             }
         }
         return instance;
     }
 
-    public static ActFmSyncThread initializeSyncComponents(TaskDao taskDao, TagDataDao tagDataDao, UserActivityDao userActivityDao) {
+    public static ActFmSyncThread initializeSyncComponents(TaskDao taskDao, TagDataDao tagDataDao, UserActivityDao userActivityDao, TaskAttachmentDao taskAttachmentDao) {
         if (instance == null) {
             synchronized(ActFmSyncThread.class) {
                 if (instance == null) {
@@ -115,6 +118,7 @@ public class ActFmSyncThread {
                     taskDao.addListener(new SyncDatabaseListener<Task>(instance, ModelType.TYPE_TASK));
                     tagDataDao.addListener(new SyncDatabaseListener<TagData>(instance, ModelType.TYPE_TAG));
                     userActivityDao.addListener(new SyncDatabaseListener<UserActivity>(instance, ModelType.TYPE_ACTIVITY));
+                    taskAttachmentDao.addListener(new SyncDatabaseListener<TaskAttachment>(instance, ModelType.TYPE_ATTACHMENT));
 
                     instance.startSyncThread();
                 }
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 e3d6e4199..55daf8c74 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
@@ -29,6 +29,8 @@ import com.todoroo.astrid.data.RemoteModel;
 import com.todoroo.astrid.data.TagData;
 import com.todoroo.astrid.data.TagOutstanding;
 import com.todoroo.astrid.data.Task;
+import com.todoroo.astrid.data.TaskAttachment;
+import com.todoroo.astrid.data.TaskAttachmentOutstanding;
 import com.todoroo.astrid.data.TaskOutstanding;
 import com.todoroo.astrid.data.UserActivity;
 import com.todoroo.astrid.data.UserActivityOutstanding;
@@ -55,6 +57,9 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
         case TYPE_ACTIVITY:
             return new ChangesHappened<UserActivity, UserActivityOutstanding>(id, UserActivity.class,
                     PluginServices.getUserActivityDao(), PluginServices.getUserActivityOutstandingDao());
+        case TYPE_ATTACHMENT:
+            return new ChangesHappened<TaskAttachment, TaskAttachmentOutstanding>(id, TaskAttachment.class,
+                    PluginServices.getTaskAttachmentDao(), PluginServices.getTaskAttachmentOutstandingDao());
         default:
             return null;
         }
diff --git a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/NameMaps.java b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/NameMaps.java
index db3c054ee..c629e69ac 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/NameMaps.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/NameMaps.java
@@ -269,7 +269,7 @@ public class NameMaps {
         TASK_ATTACHMENT_PROPERTIES_EXCLUDED = new HashSet<String>();
 
         putTaskAttachmentPropertyToServerName(TaskAttachment.UUID,         "uuid",         false);
-        putTaskAttachmentPropertyToServerName(TaskAttachment.USER_UUID,    "user_id",      true);
+        putTaskAttachmentPropertyToServerName(TaskAttachment.USER_UUID,    "user_id",      false);
         putTaskAttachmentPropertyToServerName(TaskAttachment.TASK_UUID,    "task_id",      true);
         putTaskAttachmentPropertyToServerName(TaskAttachment.NAME,         "name",         false);
         putTaskAttachmentPropertyToServerName(TaskAttachment.URL,          "url",          false);
diff --git a/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java b/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java
index 684f1dbc3..e5db9c216 100644
--- a/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java
+++ b/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java
@@ -57,12 +57,13 @@ public class TaskAttachmentDao extends RemoteModelDao<TaskAttachment> {
                 JSONObject newFileHash = new JSONObject();
                 newFileHash.put("name", modelSetValues.getAsString(TaskAttachment.NAME.name)); //$NON-NLS-1$
                 newFileHash.put("type", modelSetValues.getAsString(TaskAttachment.CONTENT_TYPE.name)); //$NON-NLS-1$
-                newFileHash.put("path", modelSetValues.getAsString(path)); //$NON-NLS-1$
+                newFileHash.put("path", path); //$NON-NLS-1$
 
                 m.setValue(OutstandingEntry.ENTITY_ID_PROPERTY, modelId);
                 m.setValue(OutstandingEntry.COLUMN_STRING_PROPERTY, NameMaps.ATTACHMENT_ADDED_COLUMN);
                 m.setValue(OutstandingEntry.VALUE_STRING_PROPERTY, newFileHash.toString());
                 m.setValue(OutstandingEntry.CREATED_AT_PROPERTY, DateUtilities.now());
+                database.insert(outstandingTable.name, null, m.getSetValues());
             } catch (JSONException e) {
                 return -1;
             }
diff --git a/astrid/src/com/todoroo/astrid/service/AstridDependencyInjector.java b/astrid/src/com/todoroo/astrid/service/AstridDependencyInjector.java
index 90143c2ab..5c16aff88 100644
--- a/astrid/src/com/todoroo/astrid/service/AstridDependencyInjector.java
+++ b/astrid/src/com/todoroo/astrid/service/AstridDependencyInjector.java
@@ -21,6 +21,8 @@ import com.todoroo.astrid.dao.StoreObjectDao;
 import com.todoroo.astrid.dao.TagDataDao;
 import com.todoroo.astrid.dao.TagMetadataDao;
 import com.todoroo.astrid.dao.TagOutstandingDao;
+import com.todoroo.astrid.dao.TaskAttachmentDao;
+import com.todoroo.astrid.dao.TaskAttachmentOutstandingDao;
 import com.todoroo.astrid.dao.TaskDao;
 import com.todoroo.astrid.dao.TaskOutstandingDao;
 import com.todoroo.astrid.dao.UpdateDao;
@@ -83,6 +85,8 @@ public class AstridDependencyInjector extends AbstractDependencyInjector {
         injectables.put("tagOutstandingDao", TagOutstandingDao.class);
         injectables.put("userActivityOutstandingDao", UserActivityOutstandingDao.class);
         injectables.put("historyDao", HistoryDao.class);
+        injectables.put("taskAttachmentDao", TaskAttachmentDao.class);
+        injectables.put("taskAttachmentOutstandingDao", TaskAttachmentOutstandingDao.class);
 
         // com.todoroo.astrid.service
         injectables.put("taskService", TaskService.class);
diff --git a/astrid/src/com/todoroo/astrid/service/StartupService.java b/astrid/src/com/todoroo/astrid/service/StartupService.java
index 877ed1406..428f71f49 100644
--- a/astrid/src/com/todoroo/astrid/service/StartupService.java
+++ b/astrid/src/com/todoroo/astrid/service/StartupService.java
@@ -52,6 +52,7 @@ import com.todoroo.astrid.core.PluginServices;
 import com.todoroo.astrid.dao.Database;
 import com.todoroo.astrid.dao.MetadataDao.MetadataCriteria;
 import com.todoroo.astrid.dao.TagDataDao;
+import com.todoroo.astrid.dao.TaskAttachmentDao;
 import com.todoroo.astrid.dao.TaskDao;
 import com.todoroo.astrid.dao.UserActivityDao;
 import com.todoroo.astrid.data.Metadata;
@@ -106,6 +107,8 @@ public class StartupService {
 
     @Autowired UserActivityDao userActivityDao;
 
+    @Autowired TaskAttachmentDao taskAttachmentDao;
+
     @Autowired MetadataService metadataService;
 
     @Autowired Database database;
@@ -221,7 +224,7 @@ public class StartupService {
         abTestInvoker.reportAcquisition();
 
         initializeDatabaseListeners();
-        ActFmSyncThread.initializeSyncComponents(taskDao, tagDataDao, userActivityDao);
+        ActFmSyncThread.initializeSyncComponents(taskDao, tagDataDao, userActivityDao, taskAttachmentDao);
 
         // perform startup activities in a background thread
         new Thread(new Runnable() {