diff --git a/nucypher/characters/lawful.py b/nucypher/characters/lawful.py
index 373f7ee43..443a131e6 100644
--- a/nucypher/characters/lawful.py
+++ b/nucypher/characters/lawful.py
@@ -1252,21 +1252,42 @@ class Ursula(Teacher, Character, Worker):
         return constants.BYTESTRING_IS_URSULA_IFACE_INFO + bytes(self)
 
     #
-    # Utilities
+    # Work Orders & Re-Encryption
     #
 
-    def work_orders(self, bob=None):
-        """
-        TODO: This is better written as a model method for Ursula's datastore.
-        """
-        if not bob:
-            return self._work_orders
-        else:
-            work_orders_from_bob = []
-            for work_order in self._work_orders:
-                if work_order.bob == bob:
-                    work_orders_from_bob.append(work_order)
-            return work_orders_from_bob
+    def work_orders(self, bob=None) -> List['WorkOrder']:
+        with ThreadedSession(self.datastore.engine):
+            if not bob:  # All
+                return self.datastore.get_workorders()
+            else:        # Filter
+                work_orders_from_bob = self.datastore.get_workorders(bob_verifying_key=bytes(bob.stamp))
+                return work_orders_from_bob
+
+    def _reencrypt(self, kfrag: KFrag, work_order: 'WorkOrder', alice_verifying_key: UmbralPublicKey):
+        
+        # Prepare a bytestring for concatenating re-encrypted
+        # capsule data for each work order task.
+        cfrag_byte_stream = bytes()
+        for task in work_order.tasks:
+
+            # Ursula signs on top of Bob's signature of each task.
+            # Now both are committed to the same task.  See #259.
+            reencryption_metadata = bytes(self.stamp(bytes(task.signature)))
+
+            # Ursula sets Alice's verifying key for capsule correctness verification.
+            capsule = task.capsule
+            capsule.set_correctness_keys(verifying=alice_verifying_key)
+
+            # Then re-encrypts the fragment.
+            cfrag = pre.reencrypt(kfrag, capsule, metadata=reencryption_metadata)  # <--- pyUmbral
+            self.log.info(f"Re-encrypted capsule {capsule} -> made {cfrag}.")
+
+            # Next, Ursula signs to commit to her results.
+            reencryption_signature = self.stamp(bytes(cfrag))
+            cfrag_byte_stream += VariableLengthBytestring(cfrag) + reencryption_signature
+
+        # ... and finally returns all the re-encrypted bytes
+        return cfrag_byte_stream
 
 
 class Enrico(Character):
diff --git a/nucypher/cli/painting.py b/nucypher/cli/painting.py
index 72cc6a1db..e6b75ddeb 100644
--- a/nucypher/cli/painting.py
+++ b/nucypher/cli/painting.py
@@ -124,7 +124,7 @@ def paint_node_status(emitter, ursula, start_time):
              'Rest Interface ...... {}'.format(ursula.rest_url()),
              'Node Storage Type ... {}'.format(ursula.node_storage._name.capitalize()),
              'Known Nodes ......... {}'.format(len(ursula.known_nodes)),
-             'Work Orders ......... {}'.format(len(ursula._work_orders)),
+             'Work Orders ......... {}'.format(len(ursula.work_orders())),
              teacher]
 
     if not ursula.federated_only:
diff --git a/nucypher/network/server.py b/nucypher/network/server.py
index ea2ce8b5e..849f6eb7c 100644
--- a/nucypher/network/server.py
+++ b/nucypher/network/server.py
@@ -291,29 +291,37 @@ def make_rest_app(
 
     @rest_app.route('/kFrag/<id_as_hex>/reencrypt', methods=["POST"])
     def reencrypt_via_rest(id_as_hex):
-        from nucypher.policy.collections import WorkOrder  # Avoid circular import
-        arrangement_id = binascii.unhexlify(id_as_hex)
+
+        # Get Policy Arrangement
+        try:
+            arrangement_id = binascii.unhexlify(id_as_hex)
+        except (binascii.Error, TypeError):
+            return Response(response=b'Invalid arrangement ID', status=405)
         try:
             with ThreadedSession(db_engine) as session:
                 arrangement = datastore.get_policy_arrangement(arrangement_id=id_as_hex.encode(), session=session)
         except NotFound:
             return Response(response=arrangement_id, status=404)
-        kfrag_bytes = policy_arrangement.kfrag  # Careful!  :-)
-        verifying_key_bytes = policy_arrangement.alice_verifying_key.key_data
 
-        # TODO: Push this to a lower level. Perhaps to Ursula character? #619
-        kfrag = KFrag.from_bytes(kfrag_bytes)
-        alices_verifying_key = UmbralPublicKey.from_bytes(verifying_key_bytes)
-        alices_address = canonical_address_from_umbral_key(alices_verifying_key)
+        # Get KFrag
+        kfrag = KFrag.from_bytes(arrangement.kfrag)  # Careful!  :-)
 
+        # Get Work Order
+        from nucypher.policy.collections import WorkOrder  # Avoid circular import
+        alice_verifying_key_bytes = arrangement.alice_verifying_key.key_data
+        alice_verifying_key = UmbralPublicKey.from_bytes(alice_verifying_key_bytes)
+        alice_address = canonical_address_from_umbral_key(alice_verifying_key)
+        work_order_payload = request.data
         work_order = WorkOrder.from_rest_payload(arrangement_id=arrangement_id,
-                                                 rest_payload=request.data,
+                                                 rest_payload=work_order_payload,
                                                  ursula=this_node,
-                                                 alice_address=alices_address)
-
+                                                 alice_address=alice_address)
         log.info(f"Work Order from {work_order.bob}, signed {work_order.receipt_signature}")
 
-        cfrag_byte_stream = b""
+        # Re-encrypt
+        response = this_node._reencrypt(kfrag=kfrag,
+                                        work_order=work_order,
+                                        alice_verifying_key=alice_verifying_key)
 
         # Now, Ursula saves this workorder to her database...
         with ThreadedSession(db_engine):
diff --git a/tests/keystore/test_keystore.py b/tests/keystore/test_keystore.py
index 524bbe56e..a8b3247f3 100644
--- a/tests/keystore/test_keystore.py
+++ b/tests/keystore/test_keystore.py
@@ -74,4 +74,4 @@ def test_workorder_sqlite_keystore(test_keystore):
     # Test del workorder
     deleted = test_keystore.del_workorders(arrangement_id)
     assert deleted > 0
-    assert test_keystore.get_workorders(arrangement_id) == 0
+    assert len(test_keystore.get_workorders(arrangement_id)) == 0