diff --git a/stdlib/2and3/imaplib.pyi b/stdlib/2and3/imaplib.pyi
index c22a47533..d24070312 100644
--- a/stdlib/2and3/imaplib.pyi
+++ b/stdlib/2and3/imaplib.pyi
@@ -5,7 +5,7 @@ import subprocess
 import sys
 import time
 from socket import socket as _socket
-from ssl import SSLSocket
+from ssl import SSLSocket, SSLContext
 from typing import Any, Callable, Dict, IO, List, Optional, Pattern, Text, Tuple, Type, Union
 
 CommandResults = Tuple[str, List[Any]]
@@ -89,7 +89,10 @@ class IMAP4:
 class IMAP4_SSL(IMAP4):
     keyfile: str = ...
     certfile: str = ...
-    def __init__(self, host: str = ..., port: int = ..., keyfile: Optional[str] = ..., certfile: Optional[str] = ...) -> None: ...
+    if sys.version_info >= (3, 3):
+        def __init__(self, host: str = ..., port: int = ..., keyfile: Optional[str] = ..., certfile: Optional[str] = ..., ssl_context: Optional[SSLContext] = ...) -> None: ...
+    else:
+        def __init__(self, host: str = ..., port: int = ..., keyfile: Optional[str] = ..., certfile: Optional[str] = ...) -> None: ...
     host: str = ...
     port: int = ...
     sock: _socket = ...