diff --git a/api/src/com/todoroo/andlib/data/Property.java b/api/src/com/todoroo/andlib/data/Property.java
index ae255c796..e481eb662 100644
--- a/api/src/com/todoroo/andlib/data/Property.java
+++ b/api/src/com/todoroo/andlib/data/Property.java
@@ -49,6 +49,8 @@ public abstract class Property<TYPE> extends Field implements Cloneable {
     public static final int PROP_FLAG_BOOLEAN = 1 << 3;
     /** Is this field a serialized JSON object? */
     public static final int PROP_FLAG_JSON = 1 << 4;
+    /** Is this field for pictures? (usually as a json object containing "path" key or urls) */
+    public static final int PROP_FLAG_PICTURE = 1 << 5;
 
     public int flags = 0;
 
diff --git a/api/src/com/todoroo/astrid/data/TagData.java b/api/src/com/todoroo/astrid/data/TagData.java
index 797f8b2d6..8002f79cc 100644
--- a/api/src/com/todoroo/astrid/data/TagData.java
+++ b/api/src/com/todoroo/astrid/data/TagData.java
@@ -63,7 +63,7 @@ public final class TagData extends RemoteModel {
 
     /** Project picture */
     public static final StringProperty PICTURE = new StringProperty(
-            TABLE, "picture", Property.PROP_FLAG_JSON);
+            TABLE, "picture", Property.PROP_FLAG_JSON | Property.PROP_FLAG_PICTURE);
 
     /** Tag team array (JSON) */
     @Deprecated public static final StringProperty MEMBERS = new StringProperty(
diff --git a/api/src/com/todoroo/astrid/data/UserActivity.java b/api/src/com/todoroo/astrid/data/UserActivity.java
index 87b9712b5..590c13e39 100644
--- a/api/src/com/todoroo/astrid/data/UserActivity.java
+++ b/api/src/com/todoroo/astrid/data/UserActivity.java
@@ -54,7 +54,7 @@ public class UserActivity extends RemoteModel {
 
     /** Picture */
     public static final StringProperty PICTURE = new StringProperty(
-            TABLE, "picture", Property.PROP_FLAG_JSON);
+            TABLE, "picture", Property.PROP_FLAG_JSON | Property.PROP_FLAG_PICTURE);
 
     /** Target id */
     public static final StringProperty TARGET_ID = new StringProperty(
diff --git a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmInvoker.java b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmInvoker.java
index 72d20a464..826376659 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmInvoker.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmInvoker.java
@@ -12,14 +12,12 @@ import java.security.NoSuchAlgorithmException;
 import java.util.ArrayList;
 import java.util.Collections;
 import java.util.Comparator;
-import java.util.List;
 import java.util.TimeZone;
 
 import org.apache.commons.codec.digest.DigestUtils;
 import org.apache.http.HttpEntity;
-import org.apache.http.client.entity.UrlEncodedFormEntity;
-import org.apache.http.message.BasicNameValuePair;
-import org.apache.http.protocol.HTTP;
+import org.apache.http.entity.mime.MultipartEntity;
+import org.apache.http.entity.mime.content.StringBody;
 import org.json.JSONArray;
 import org.json.JSONException;
 import org.json.JSONObject;
@@ -185,7 +183,7 @@ public class ActFmInvoker {
         }
     }
 
-    public JSONObject postSync(JSONArray data, String token) throws IOException,
+    public JSONObject postSync(JSONArray data, MultipartEntity entity, String token) throws IOException,
     ActFmServiceException {
         try {
             String dataString = data.toString();
@@ -194,11 +192,9 @@ public class ActFmInvoker {
             String request = createFetchUrl("api/" + API_VERSION, "synchronize", "token", token, "data", dataString, "time", timeString);
             if (SYNC_DEBUG)
                 Log.e("act-fm-post", request);
-            List<BasicNameValuePair> pairs = new ArrayList<BasicNameValuePair>();
-            pairs.add(new BasicNameValuePair("token", token));
-            pairs.add(new BasicNameValuePair("data", data.toString()));
-            pairs.add(new BasicNameValuePair("time", timeString));
-            UrlEncodedFormEntity entity = new UrlEncodedFormEntity(pairs, HTTP.UTF_8);
+            entity.addPart("token", new StringBody(token));
+            entity.addPart("data", new StringBody(data.toString()));
+            entity.addPart("time", new StringBody(timeString));
 
             String response = restClient.post(request, entity);
             JSONObject object = new JSONObject(response);
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 0dbf3531e..b35901526 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmSyncThread.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/ActFmSyncThread.java
@@ -9,6 +9,7 @@ import java.util.List;
 import java.util.Map;
 import java.util.Set;
 
+import org.apache.http.entity.mime.MultipartEntity;
 import org.json.JSONArray;
 import org.json.JSONObject;
 
@@ -295,8 +296,9 @@ public class ActFmSyncThread {
 
                 if (!messageBatch.isEmpty() && checkForToken()) {
                     JSONArray payload = new JSONArray();
+                    MultipartEntity entity = new MultipartEntity();
                     for (ClientToServerMessage<?> message : messageBatch) {
-                        JSONObject serialized = message.serializeToJSON();
+                        JSONObject serialized = message.serializeToJSON(entity);
                         if (serialized != null) {
                             payload.put(serialized);
                             syncLog("Sending: " + serialized);
@@ -309,7 +311,7 @@ public class ActFmSyncThread {
                         continue;
 
                     try {
-                        JSONObject response = actFmInvoker.postSync(payload, token);
+                        JSONObject response = actFmInvoker.postSync(payload, entity, token);
                         // process responses
                         JSONArray serverMessagesJson = response.optJSONArray("messages");
                         if (serverMessagesJson != null) {
diff --git a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/BriefMe.java b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/BriefMe.java
index 4cfb89933..7c74ee98f 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/BriefMe.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/BriefMe.java
@@ -1,5 +1,6 @@
 package com.todoroo.astrid.actfm.sync.messages;
 
+import org.apache.http.entity.mime.MultipartEntity;
 import org.json.JSONException;
 import org.json.JSONObject;
 
@@ -34,7 +35,7 @@ public class BriefMe<TYPE extends RemoteModel> extends ClientToServerMessage<TYP
     }
 
     @Override
-    protected boolean serializeExtrasToJSON(JSONObject serializeTo) throws JSONException {
+    protected boolean serializeExtrasToJSON(JSONObject serializeTo, MultipartEntity entity) throws JSONException {
         if (extraParameters != null && extraParameters.length > 0) {
             for (int i = 0; i < extraParameters.length - 1; i++) {
                 try {
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 aa16200a2..acddf7607 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
@@ -4,6 +4,8 @@ import java.io.File;
 import java.util.ArrayList;
 import java.util.List;
 
+import org.apache.http.entity.mime.MultipartEntity;
+import org.apache.http.entity.mime.content.FileBody;
 import org.json.JSONArray;
 import org.json.JSONException;
 import org.json.JSONObject;
@@ -80,9 +82,9 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
     }
 
     @Override
-    protected boolean serializeExtrasToJSON(JSONObject serializeTo) throws JSONException {
+    protected boolean serializeExtrasToJSON(JSONObject serializeTo, MultipartEntity entity) throws JSONException {
         // Process changes list and serialize to JSON
-        JSONArray changesJson = changesToJSON();
+        JSONArray changesJson = changesToJSON(entity);
         if (changesJson == null || changesJson.length() == 0)
             return false;
         serializeTo.put(CHANGES_KEY, changesJson);
@@ -98,7 +100,7 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
         return changes;
     }
 
-    private JSONArray changesToJSON() {
+    private JSONArray changesToJSON(MultipartEntity entity) {
         if (!RemoteModel.NO_UUID.equals(uuid))
             populateChanges();
 
@@ -146,8 +148,21 @@ public class ChangesHappened<TYPE extends RemoteModel, OE extends OutstandingEnt
 
                     if (value == null)
                         changeJson.put("value", JSONObject.NULL);
-                    else
+                    else {
+                        if (localProperty.checkFlag(Property.PROP_FLAG_PICTURE) && value instanceof JSONObject) {
+                            JSONObject json = (JSONObject) value;
+                            if (json.has("path")) {
+                                String path = json.optString("path");
+                                String name = json.optString("name");
+                                File f = new File(path);
+                                if (f.exists() && !TextUtils.isEmpty(name)) {
+                                    json.remove("path");
+                                    entity.addPart(name, new FileBody(f));
+                                }
+                            }
+                        }
                         changeJson.put("value", value);
+                    }
                 }
 
                 changeJson.put("column", serverColumn);
diff --git a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ClientToServerMessage.java b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ClientToServerMessage.java
index c1a3eca39..ce13a7ea2 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ClientToServerMessage.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/ClientToServerMessage.java
@@ -1,5 +1,6 @@
 package com.todoroo.astrid.actfm.sync.messages;
 
+import org.apache.http.entity.mime.MultipartEntity;
 import org.json.JSONException;
 import org.json.JSONObject;
 
@@ -61,7 +62,7 @@ public abstract class ClientToServerMessage<TYPE extends RemoteModel> {
         return pushedAt;
     }
 
-    public final JSONObject serializeToJSON() {
+    public final JSONObject serializeToJSON(MultipartEntity entity) {
         JSONObject json = new JSONObject();
         try {
             json.put(TYPE_KEY, getTypeString());
@@ -69,7 +70,7 @@ public abstract class ClientToServerMessage<TYPE extends RemoteModel> {
             json.put(UUID_KEY, uuid);
             String dateValue = DateUtilities.timeToIso8601(pushedAt, true);
             json.put(PUSHED_AT_KEY, dateValue != null ? dateValue : 0);
-            if (serializeExtrasToJSON(json))
+            if (serializeExtrasToJSON(json, entity))
                 return json;
             else
                 return null;
@@ -109,6 +110,6 @@ public abstract class ClientToServerMessage<TYPE extends RemoteModel> {
         return true;
     }
 
-    protected abstract boolean serializeExtrasToJSON(JSONObject serializeTo) throws JSONException;
+    protected abstract boolean serializeExtrasToJSON(JSONObject serializeTo, MultipartEntity entity) throws JSONException;
     protected abstract String getTypeString();
 }
diff --git a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/RequestDoubleCheck.java b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/RequestDoubleCheck.java
index 0f70b0da8..5f405f783 100644
--- a/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/RequestDoubleCheck.java
+++ b/astrid/plugin-src/com/todoroo/astrid/actfm/sync/messages/RequestDoubleCheck.java
@@ -1,5 +1,6 @@
 package com.todoroo.astrid.actfm.sync.messages;
 
+import org.apache.http.entity.mime.MultipartEntity;
 import org.json.JSONException;
 import org.json.JSONObject;
 
@@ -13,7 +14,7 @@ public class RequestDoubleCheck<TYPE extends RemoteModel> extends ClientToServer
     }
 
     @Override
-    protected boolean serializeExtrasToJSON(JSONObject serializeTo) throws JSONException {
+    protected boolean serializeExtrasToJSON(JSONObject serializeTo, MultipartEntity entity) throws JSONException {
         // No extras
         return true;
     }