diff --git a/telethon/extensions/tcp_client.py b/telethon/extensions/tcp_client.py
index 2ccdb0f0..edf6cb4b 100644
--- a/telethon/extensions/tcp_client.py
+++ b/telethon/extensions/tcp_client.py
@@ -30,19 +30,33 @@ class TcpClient:
             else:  # tuple, list, etc.
                 self._socket.set_proxy(*self._proxy)
 
+        self._socket.settimeout(self._timeout)
+
     def connect(self, ip, port):
         """Connects to the specified IP and port number.
            'timeout' must be given in seconds
         """
-        if not self.connected:
-            if ':' in ip:  # IPv6
-                mode, address = socket.AF_INET6, (ip, port, 0, 0)
-            else:
-                mode, address = socket.AF_INET, (ip, port)
+        if ':' in ip:  # IPv6
+            mode, address = socket.AF_INET6, (ip, port, 0, 0)
+        else:
+            mode, address = socket.AF_INET, (ip, port)
 
-            self._recreate_socket(mode)
-            self._socket.settimeout(self._timeout)
-            self._socket.connect(address)
+        while True:
+            try:
+                if not self._socket:
+                    self._recreate_socket(mode)
+
+                self._socket.connect(address)
+                break  # Successful connection, stop retrying to connect
+            except OSError as e:
+                # There are some errors that we know how to handle, and
+                # the loop will allow us to retry
+                if e.errno == errno.EBADF:
+                    # Bad file descriptor, i.e. socket was closed, set it
+                    # to none to recreate it on the next iteration
+                    self._socket = None
+                else:
+                    raise
 
     def _get_connected(self):
         return self._socket is not None
diff --git a/telethon/network/connection.py b/telethon/network/connection.py
index 1426ce78..c79703cf 100644
--- a/telethon/network/connection.py
+++ b/telethon/network/connection.py
@@ -3,6 +3,8 @@ from datetime import timedelta
 from zlib import crc32
 from enum import Enum
 
+import errno
+
 from ..crypto import AESModeCTR
 from ..extensions import BinaryWriter, TcpClient
 from ..errors import InvalidChecksumError
@@ -75,9 +77,15 @@ class Connection:
             setattr(self, 'read', self._read_plain)
 
     def connect(self):
-        self._send_counter = 0
-        self.conn.connect(self.ip, self.port)
+        try:
+            self.conn.connect(self.ip, self.port)
+        except OSError as e:
+            if e.errno == errno.EISCONN:
+                return  # Already connected, no need to re-set everything up
+            else:
+                raise
 
+        self._send_counter = 0
         if self._mode == ConnectionMode.TCP_ABRIDGED:
             self.conn.write(b'\xef')
         elif self._mode == ConnectionMode.TCP_INTERMEDIATE: