diff --git a/pantalaimon/client.py b/pantalaimon/client.py
index 807c7dc..466f874 100644
--- a/pantalaimon/client.py
+++ b/pantalaimon/client.py
@@ -54,7 +54,7 @@ class PanClient(AsyncClient):
         self.key_request_tasks = []
 
         self.add_response_callback(
-            self.verify_devices,
+            self.keys_query_cb,
             KeysQueryResponse
         )
 
@@ -90,8 +90,7 @@ class PanClient(AsyncClient):
         self.key_verificatins_tasks = []
         self.key_request_tasks = []
 
-    async def verify_devices(self, response):
-        # Verify new devices automatically for now.
+    async def keys_query_cb(self, response):
         changed_devices = response.changed
 
         for user_id, device_dict in changed_devices.items():
diff --git a/pantalaimon/daemon.py b/pantalaimon/daemon.py
index 92236d8..d0cf1ac 100755
--- a/pantalaimon/daemon.py
+++ b/pantalaimon/daemon.py
@@ -13,7 +13,8 @@ from aiohttp import ClientSession, web
 from aiohttp.client_exceptions import (ContentTypeError,
                                        ClientConnectionError)
 from multidict import CIMultiDict
-from nio import EncryptionError, GroupEncryptionError, LoginResponse
+from nio import (EncryptionError, GroupEncryptionError, LoginResponse,
+                 MembersSyncError)
 
 from pantalaimon.client import PanClient
 from pantalaimon.log import logger
@@ -26,10 +27,14 @@ from pantalaimon.thread_messages import (
     DeviceConfirmSasMessage,
     SasMessage,
     AcceptSasMessage,
-    DaemonResponse
+    DaemonResponse,
 )
 
 
+class SendError(Exception):
+    pass
+
+
 @attr.s
 class ProxyDaemon:
     name = attr.ib()
@@ -615,6 +620,24 @@ class ProxyDaemon:
             body=await response.read()
         )
 
+    async def _send_message(self, client, room_id, msgtype, content, txnid):
+        """Send a room message, fetch room members and share group sessions."""
+        retries = 5
+
+        for i in range(retries):
+            try:
+                return await client.room_send(room_id, msgtype, content, txnid)
+            except GroupEncryptionError:
+                await client.share_group_session(room_id)
+            except MembersSyncError:
+                await client.joined_members(room_id)
+
+                if client.should_query_keys:
+                    keys_query_response = await client.keys_query()
+                    await client.keys_query_cb(keys_query_response)
+
+        raise SendError("Service Unavailable")
+
     async def send_message(self, request):
         access_token = self.get_access_token(request)
 
@@ -649,12 +672,12 @@ class ProxyDaemon:
             return self._not_json
 
         try:
-            response = await client.room_send(room_id, msgtype, content, txnid)
-        except GroupEncryptionError:
-            await client.share_group_session(room_id)
-            response = await client.room_send(room_id, msgtype, content, txnid)
+            response = await self._send_message(client, room_id, msgtype,
+                                                content, txnid)
         except ClientConnectionError as e:
             return web.Response(status=500, text=str(e))
+        except SendError as e:
+            return web.Response(status=503, text=str(e))
 
         return web.Response(
             status=response.transport_response.status,