diff --git a/api/src/com/todoroo/andlib/utility/AndroidUtilities.java b/api/src/com/todoroo/andlib/utility/AndroidUtilities.java
index 09b2bf05d..1f0a9fb53 100644
--- a/api/src/com/todoroo/andlib/utility/AndroidUtilities.java
+++ b/api/src/com/todoroo/andlib/utility/AndroidUtilities.java
@@ -10,6 +10,7 @@ import java.io.BufferedReader;
 import java.io.ByteArrayOutputStream;
 import java.io.File;
 import java.io.FileInputStream;
+import java.io.FileNotFoundException;
 import java.io.FileOutputStream;
 import java.io.IOException;
 import java.io.InputStream;
@@ -153,6 +154,32 @@ public class AndroidUtilities {
         return BitmapFactory.decodeByteArray(decodedByte, 0, decodedByte.length);
     }
 
+
+    private static final int BUFFER_SIZE = 4096;
+    public static String encodeBase64File(File file) {
+        try {
+            FileInputStream in = new FileInputStream(file);
+            try {
+            ByteArrayOutputStream baos = new ByteArrayOutputStream();
+
+            byte[] buffer = new byte[BUFFER_SIZE];
+            int len = 0;
+            while ((len = in.read(buffer)) > 0) {
+                baos.write(buffer, 0, len);
+            }
+
+            byte[] bytes = baos.toByteArray();
+            return Base64.encodeToString(bytes, Base64.DEFAULT);
+            } finally {
+                in.close();
+            }
+        } catch (FileNotFoundException e) {
+            return null;
+        } catch (IOException e) {
+            return null;
+        }
+    }
+
     /**
      * Start the given intent, handling security exceptions if they arise
      *
diff --git a/api/src/com/todoroo/astrid/data/TaskAttachment.java b/api/src/com/todoroo/astrid/data/TaskAttachment.java
index 1941eb565..784d5f247 100644
--- a/api/src/com/todoroo/astrid/data/TaskAttachment.java
+++ b/api/src/com/todoroo/astrid/data/TaskAttachment.java
@@ -144,6 +144,7 @@ public final class TaskAttachment extends RemoteModel {
         TaskAttachment attachment = new TaskAttachment();
         attachment.setValue(TaskAttachment.TASK_UUID, taskUuid);
         attachment.setValue(NAME, fileName);
+        attachment.setValue(USER_UUID, Task.USER_ID_SELF);
         attachment.setValue(FILE_PATH, filePath);
         attachment.setValue(CONTENT_TYPE, fileType);
         attachment.setValue(DELETED_AT, 0L);
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 4c8662146..e3d6e4199 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
@@ -1,5 +1,6 @@
 package com.todoroo.astrid.actfm.sync.messages;
 
+import java.io.File;
 import java.util.ArrayList;
 import java.util.List;
 
@@ -7,6 +8,7 @@ import org.json.JSONArray;
 import org.json.JSONException;
 import org.json.JSONObject;
 
+import android.text.TextUtils;
 import android.util.Log;
 
 import com.todoroo.andlib.data.Property;
@@ -14,6 +16,7 @@ import com.todoroo.andlib.data.Property.PropertyVisitor;
 import com.todoroo.andlib.data.TodorooCursor;
 import com.todoroo.andlib.sql.Order;
 import com.todoroo.andlib.sql.Query;
+import com.todoroo.andlib.utility.AndroidUtilities;
 import com.todoroo.andlib.utility.DateUtilities;
 import com.todoroo.astrid.actfm.sync.ActFmPreferenceService;
 import com.todoroo.astrid.actfm.sync.ActFmSyncThread.ModelType;
@@ -110,6 +113,15 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
                 } else if (NameMaps.MEMBER_REMOVED_COLUMN.equals(localColumn)) {
                     serverColumn = NameMaps.MEMBER_REMOVED_COLUMN;
                     changeJson.put("value", change.getValue(OutstandingEntry.VALUE_STRING_PROPERTY));
+                } else if (NameMaps.ATTACHMENT_ADDED_COLUMN.equals(localColumn)) {
+                    serverColumn = NameMaps.ATTACHMENT_ADDED_COLUMN;
+                    JSONObject fileJson = getFileJson(change.getValue(OutstandingEntry.VALUE_STRING_PROPERTY));
+                    if (fileJson == null) {
+                        PluginServices.getTaskAttachmentDao().delete(id);
+                        continue;
+                    } else {
+                        changeJson.put("value", fileJson.toString());
+                    }
                 } else {
                     Property<?> localProperty = NameMaps.localColumnNameToProperty(table, localColumn);
                     if (localProperty == null)
@@ -155,6 +167,28 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
         }
     }
 
+    private JSONObject getFileJson(String value) {
+        try {
+            JSONObject obj = new JSONObject(value);
+            String path = obj.optString("path");
+            if (TextUtils.isEmpty(path))
+                return null;
+            File f = new File(path);
+            if (!f.exists())
+                return null;
+
+            String encodedFile = AndroidUtilities.encodeBase64File(f);
+            if (TextUtils.isEmpty(encodedFile))
+                return null;
+
+            obj.remove("path");
+            obj.put("data", encodedFile);
+            return obj;
+        } catch (JSONException e) {
+            return null;
+        }
+    }
+
     private class PropertyToJSONVisitor implements PropertyVisitor<Object, OE> {
 
         private String getAsString(OE data) {
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 ccd635afc..db3c054ee 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
@@ -255,6 +255,8 @@ public class NameMaps {
     private static final Map<String, Property<?>> TASK_ATTACHMENT_PROPERTIES_SERVER_TO_LOCAL;
     private static final Set<String> TASK_ATTACHMENT_PROPERTIES_EXCLUDED;
 
+    public static final String ATTACHMENT_ADDED_COLUMN = "file";
+
     private static void putTaskAttachmentPropertyToServerName(Property<?> property, String serverName, boolean writeable) {
         putPropertyToServerName(property, serverName, TASK_ATTACHMENT_PROPERTIES_LOCAL_TO_SERVER, TASK_ATTACHMENT_COLUMN_NAMES_TO_PROPERTIES,
                 TASK_ATTACHMENT_COLUMNS_LOCAL_TO_SERVER, TASK_ATTACHMENT_PROPERTIES_EXCLUDED, writeable);
diff --git a/astrid/plugin-src/com/todoroo/astrid/files/FilesControlSet.java b/astrid/plugin-src/com/todoroo/astrid/files/FilesControlSet.java
index 578e211ca..b63689cd1 100644
--- a/astrid/plugin-src/com/todoroo/astrid/files/FilesControlSet.java
+++ b/astrid/plugin-src/com/todoroo/astrid/files/FilesControlSet.java
@@ -46,6 +46,7 @@ import com.todoroo.andlib.utility.DialogUtilities;
 import com.todoroo.astrid.actfm.sync.ActFmPreferenceService;
 import com.todoroo.astrid.dao.TaskAttachmentDao;
 import com.todoroo.astrid.data.RemoteModel;
+import com.todoroo.astrid.data.SyncFlags;
 import com.todoroo.astrid.data.Task;
 import com.todoroo.astrid.data.TaskAttachment;
 import com.todoroo.astrid.ui.PopupControlSet;
@@ -256,6 +257,7 @@ public class FilesControlSet extends PopupControlSet {
                     useType = guessedType;
                 if (useType != guessedType) {
                     m.setValue(TaskAttachment.CONTENT_TYPE, useType);
+                    m.putTransitory(SyncFlags.ACTFM_SUPPRESS_OUTSTANDING_ENTRIES, true);
                     taskAttachmentDao.saveExisting(m);
                 }
             }
diff --git a/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java b/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java
index 1499c570a..684f1dbc3 100644
--- a/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java
+++ b/astrid/src/com/todoroo/astrid/dao/TaskAttachmentDao.java
@@ -5,14 +5,23 @@
  */
 package com.todoroo.astrid.dao;
 
+import org.json.JSONException;
+import org.json.JSONObject;
+
+import android.content.ContentValues;
+import android.text.TextUtils;
+
 import com.todoroo.andlib.data.TodorooCursor;
 import com.todoroo.andlib.service.Autowired;
 import com.todoroo.andlib.service.DependencyInjectionService;
 import com.todoroo.andlib.sql.Criterion;
 import com.todoroo.andlib.sql.Query;
+import com.todoroo.andlib.utility.DateUtilities;
 import com.todoroo.astrid.actfm.sync.messages.NameMaps;
+import com.todoroo.astrid.data.OutstandingEntry;
 import com.todoroo.astrid.data.TagData;
 import com.todoroo.astrid.data.TaskAttachment;
+import com.todoroo.astrid.data.TaskAttachmentOutstanding;
 
 /**
  * Data Access layer for {@link TagData}-related operations.
@@ -36,6 +45,34 @@ public class TaskAttachmentDao extends RemoteModelDao<TaskAttachment> {
         return NameMaps.shouldRecordOutstandingColumnForTable(NameMaps.TABLE_ID_ATTACHMENTS, columnName);
     }
 
+    @Override
+    protected int createOutstandingEntries(long modelId, ContentValues modelSetValues) {
+        // new attachment case -- only set by us when creating new attachments; when setting during sync outstanding entries suppressed
+        if (modelSetValues.containsKey(TaskAttachment.CONTENT_TYPE.name)) {
+            TaskAttachmentOutstanding m = new TaskAttachmentOutstanding();
+            String path = modelSetValues.getAsString(TaskAttachment.FILE_PATH.name);
+            if (TextUtils.isEmpty(path))
+                return -1;
+            try {
+                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)); //$NON-NLS-1$
+
+                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());
+            } catch (JSONException e) {
+                return -1;
+            }
+        }
+        int result = super.createOutstandingEntries(modelId, modelSetValues);
+        if (result < 0) // Error
+            return result;
+        return 1 + result;
+    }
+
     public boolean taskHasAttachments(String taskUuid) {
         TodorooCursor<TaskAttachment> files = query(Query.select(TaskAttachment.TASK_UUID).where(
                         Criterion.and(TaskAttachment.TASK_UUID.eq(taskUuid),