diff --git a/telethon/interactive_telegram_client.py b/telethon/interactive_telegram_client.py
index e9d32dae..b24c6b0f 100644
--- a/telethon/interactive_telegram_client.py
+++ b/telethon/interactive_telegram_client.py
@@ -51,7 +51,11 @@ class InteractiveTelegramClient(TelegramClient):
         self.found_media = set()
 
         print('Connecting to Telegram servers...')
-        self.connect()
+        if not self.connect():
+            print('Initial connection failed. Retrying...')
+            if not self.connect():
+                print('Could not connect to Telegram servers.')
+                return
 
         # Then, ensure we're authorized and have access
         if not self.is_user_authorized():
diff --git a/telethon/telegram_client.py b/telethon/telegram_client.py
index 81ee707e..70c5d790 100644
--- a/telethon/telegram_client.py
+++ b/telethon/telegram_client.py
@@ -147,7 +147,8 @@ class TelegramClient:
                 self._setup_ping_thread()
 
             return True
-        except RPCError as error:
+        except (RPCError, ConnectionError) as error:
+            # Probably errors from the previous session, ignore them
             self._logger.warning('Could not stabilise initial connection: {}'
                                  .format(error))
             return False
@@ -163,7 +164,7 @@ class TelegramClient:
             self.transport = None
 
         # Also disconnect all the cached senders
-        for sender in self._cached_senders:
+        for sender in self._cached_senders.values():
             sender.disconnect()
 
         self._cached_senders.clear()
@@ -196,7 +197,7 @@ class TelegramClient:
         if not self.dc_options:
             raise ConnectionError(
                 'Cannot determine the required data center IP address. '
-                'Stabilise an initial connection first.')
+                'Stabilise a successful initial connection first.')
 
         return next(dc for dc in self.dc_options if dc.id == dc_id)
 
@@ -218,8 +219,8 @@ class TelegramClient:
 
         if sender and session:
             if init_connection:
-                # TODO reconnect
-                pass
+                sender.disconnect()
+                sender.connect()
 
             return sender
         else: