From 46f2965d3b9ad56be27df4646792c014253eb954 Mon Sep 17 00:00:00 2001
From: donbarbos <donbarbos@proton.me>
Date: Sun, 11 Jan 2026 17:48:49 +0400
Subject: [PATCH 1/4] [stdlib] Deprecate keyfile, certfile and check_hostname
 parameters

Source: https://github.com/python/cpython/pull/94173
---
 stdlib/ftplib.pyi      | 28 +++++++++++++++++++++++-----
 stdlib/http/client.pyi | 18 ++++++++++++++++++
 stdlib/imaplib.pyi     | 11 ++++++++++-
 stdlib/poplib.pyi      | 11 ++++++++++-
 stdlib/smtplib.pyi     | 29 ++++++++++++++++++++++++++---
 5 files changed, 87 insertions(+), 10 deletions(-)

diff --git a/stdlib/ftplib.pyi b/stdlib/ftplib.pyi
index 44bc2165fe0e..df6d22f0e216 100644
--- a/stdlib/ftplib.pyi
+++ b/stdlib/ftplib.pyi
@@ -4,8 +4,8 @@ from collections.abc import Callable, Iterable, Iterator
 from socket import socket
 from ssl import SSLContext
 from types import TracebackType
-from typing import Any, Final, Literal, TextIO
-from typing_extensions import Self
+from typing import Any, Final, Literal, TextIO, overload
+from typing_extensions import Self, deprecated
 
 __all__ = ["FTP", "error_reply", "error_temp", "error_perm", "error_proto", "all_errors", "FTP_TLS"]
 
@@ -120,6 +120,24 @@ class FTP_TLS(FTP):
             encoding: str = "utf-8",
         ) -> None: ...
     else:
+        @overload
+        def __init__(
+            self,
+            host: str = "",
+            user: str = "",
+            passwd: str = "",
+            acct: str = "",
+            *,
+            context: SSLContext | None = None,
+            timeout: float | None = ...,
+            source_address: tuple[str, int] | None = None,
+            encoding: str = "utf-8",
+        ) -> None: ...
+        @overload
+        @deprecated(
+            "The `keyfile`, `certfile` parameters are deprecated since Python 3.6; "
+            "removed in Python 3.12. Use `context` parameter instead."
+        )
         def __init__(
             self,
             host: str = "",
@@ -134,9 +152,9 @@ class FTP_TLS(FTP):
             *,
             encoding: str = "utf-8",
         ) -> None: ...
-    ssl_version: int
-    keyfile: str | None
-    certfile: str | None
+        ssl_version: int
+        keyfile: str | None
+        certfile: str | None
     context: SSLContext
     def login(self, user: str = "", passwd: str = "", acct: str = "", secure: bool = True) -> str: ...
     def auth(self) -> str: ...
diff --git a/stdlib/http/client.pyi b/stdlib/http/client.pyi
index 1ae63c76bf3a..54a188d0dd14 100644
--- a/stdlib/http/client.pyi
+++ b/stdlib/http/client.pyi
@@ -223,6 +223,22 @@ class HTTPSConnection(HTTPConnection):
             blocksize: int = 8192,
         ) -> None: ...
     else:
+        @overload
+        def __init__(
+            self,
+            host: str,
+            port: int | None = None,
+            timeout: float | None = ...,
+            source_address: tuple[str, int] | None = None,
+            *,
+            context: ssl.SSLContext | None = None,
+            blocksize: int = 8192,
+        ) -> None: ...
+        @overload
+        @deprecated(
+            "The `key_file`, `cert_file`, `check_hostname` parameters are deprecated since Python 3.6; "
+            "removed in Python 3.12. Use `context` parameter instead."
+        )
         def __init__(
             self,
             host: str,
@@ -236,6 +252,8 @@ class HTTPSConnection(HTTPConnection):
             check_hostname: bool | None = None,
             blocksize: int = 8192,
         ) -> None: ...
+        key_file: str | None
+        cert_file: str | None
 
 class HTTPException(Exception): ...
 
diff --git a/stdlib/imaplib.pyi b/stdlib/imaplib.pyi
index 1f0e0106006b..6fe123519d63 100644
--- a/stdlib/imaplib.pyi
+++ b/stdlib/imaplib.pyi
@@ -9,7 +9,7 @@ from re import Pattern
 from socket import socket as _socket
 from ssl import SSLContext, SSLSocket
 from types import TracebackType
-from typing import IO, Any, Literal, SupportsAbs, SupportsInt
+from typing import IO, Any, Literal, SupportsAbs, SupportsInt, overload
 from typing_extensions import Self, TypeAlias, deprecated
 
 __all__ = ["IMAP4", "IMAP4_stream", "Internaldate2tuple", "Int2AP", "ParseFlags", "Time2Internaldate", "IMAP4_SSL"]
@@ -128,6 +128,15 @@ class IMAP4_SSL(IMAP4):
             self, host: str = "", port: int = 993, *, ssl_context: SSLContext | None = None, timeout: float | None = None
         ) -> None: ...
     else:
+        @overload
+        def __init__(
+            self, host: str = "", port: int = 993, *, ssl_context: SSLContext | None = None, timeout: float | None = None
+        ) -> None: ...
+        @overload
+        @deprecated(
+            "The `keyfile`, `certfile` parameters are deprecated since Python 3.6; "
+            "removed in Python 3.12. Use `ssl_context` parameter instead."
+        )
         def __init__(
             self,
             host: str = "",
diff --git a/stdlib/poplib.pyi b/stdlib/poplib.pyi
index 9ff2b764aeb6..658ff57e6040 100644
--- a/stdlib/poplib.pyi
+++ b/stdlib/poplib.pyi
@@ -4,7 +4,7 @@ import sys
 from builtins import list as _list  # conflicts with a method named "list"
 from re import Pattern
 from typing import Any, BinaryIO, Final, NoReturn, overload
-from typing_extensions import TypeAlias
+from typing_extensions import TypeAlias, deprecated
 
 __all__ = ["POP3", "error_proto", "POP3_SSL"]
 
@@ -58,6 +58,15 @@ class POP3_SSL(POP3):
         ) -> None: ...
         def stls(self, context: Any = None) -> NoReturn: ...
     else:
+        @overload
+        def __init__(
+            self, host: str, port: int = 995, *, timeout: float = ..., context: ssl.SSLContext | None = None
+        ) -> None: ...
+        @overload
+        @deprecated(
+            "The `keyfile`, `certfile` parameters are deprecated since Python 3.6; "
+            "removed in Python 3.12. Use `context` parameter instead."
+        )
         def __init__(
             self,
             host: str,
diff --git a/stdlib/smtplib.pyi b/stdlib/smtplib.pyi
index 6a8467689367..431e8c8eea8a 100644
--- a/stdlib/smtplib.pyi
+++ b/stdlib/smtplib.pyi
@@ -8,7 +8,7 @@ from socket import socket
 from ssl import SSLContext
 from types import TracebackType
 from typing import Any, Final, Protocol, overload, type_check_only
-from typing_extensions import Self, TypeAlias
+from typing_extensions import Self, TypeAlias, deprecated
 
 __all__ = [
     "SMTPException",
@@ -131,6 +131,13 @@ class SMTP:
     if sys.version_info >= (3, 12):
         def starttls(self, *, context: SSLContext | None = None) -> _Reply: ...
     else:
+        @overload
+        def starttls(self, *, context: SSLContext | None = None) -> _Reply: ...
+        @overload
+        @deprecated(
+            "The `keyfile`, `certfile` parameters are deprecated since Python 3.6; "
+            "removed in Python 3.12. Use `context` parameter instead."
+        )
         def starttls(
             self, keyfile: str | None = None, certfile: str | None = None, context: SSLContext | None = None
         ) -> _Reply: ...
@@ -155,8 +162,6 @@ class SMTP:
     def quit(self) -> _Reply: ...
 
 class SMTP_SSL(SMTP):
-    keyfile: str | None
-    certfile: str | None
     context: SSLContext
     if sys.version_info >= (3, 12):
         def __init__(
@@ -170,6 +175,22 @@ class SMTP_SSL(SMTP):
             context: SSLContext | None = None,
         ) -> None: ...
     else:
+        @overload
+        def __init__(
+            self,
+            host: str = "",
+            port: int = 0,
+            local_hostname: str | None = None,
+            *,
+            timeout: float = ...,
+            source_address: _SourceAddress | None = None,
+            context: SSLContext | None = None,
+        ) -> None: ...
+        @overload
+        @deprecated(
+            "The `keyfile`, `certfile` parameters are deprecated since Python 3.6; "
+            "removed in Python 3.12. Use `context` parameter instead."
+        )
         def __init__(
             self,
             host: str = "",
@@ -181,6 +202,8 @@ class SMTP_SSL(SMTP):
             source_address: _SourceAddress | None = None,
             context: SSLContext | None = None,
         ) -> None: ...
+        keyfile: str | None
+        certfile: str | None
 
 LMTP_PORT: Final = 2003
 

From 24e1b9c1139d159a4b3095c7afe09860775b6582 Mon Sep 17 00:00:00 2001
From: donbarbos <donbarbos@proton.me>
Date: Sun, 11 Jan 2026 18:08:20 +0400
Subject: [PATCH 2/4] Use StrOrBytesPath

---
 stdlib/ftplib.pyi      | 10 +++++-----
 stdlib/http/client.pyi | 10 +++++-----
 stdlib/imaplib.pyi     | 11 +++++------
 stdlib/poplib.pyi      |  7 +++++--
 stdlib/smtplib.pyi     | 12 ++++++------
 5 files changed, 26 insertions(+), 24 deletions(-)

diff --git a/stdlib/ftplib.pyi b/stdlib/ftplib.pyi
index df6d22f0e216..2558cbec7cd5 100644
--- a/stdlib/ftplib.pyi
+++ b/stdlib/ftplib.pyi
@@ -1,5 +1,5 @@
 import sys
-from _typeshed import SupportsRead, SupportsReadline
+from _typeshed import StrOrBytesPath, SupportsRead, SupportsReadline
 from collections.abc import Callable, Iterable, Iterator
 from socket import socket
 from ssl import SSLContext
@@ -144,8 +144,8 @@ class FTP_TLS(FTP):
             user: str = "",
             passwd: str = "",
             acct: str = "",
-            keyfile: str | None = None,
-            certfile: str | None = None,
+            keyfile: StrOrBytesPath | None = None,
+            certfile: StrOrBytesPath | None = None,
             context: SSLContext | None = None,
             timeout: float | None = ...,
             source_address: tuple[str, int] | None = None,
@@ -153,8 +153,8 @@ class FTP_TLS(FTP):
             encoding: str = "utf-8",
         ) -> None: ...
         ssl_version: int
-        keyfile: str | None
-        certfile: str | None
+        keyfile: StrOrBytesPath | None
+        certfile: StrOrBytesPath | None
     context: SSLContext
     def login(self, user: str = "", passwd: str = "", acct: str = "", secure: bool = True) -> str: ...
     def auth(self) -> str: ...
diff --git a/stdlib/http/client.pyi b/stdlib/http/client.pyi
index 54a188d0dd14..e01c0165a151 100644
--- a/stdlib/http/client.pyi
+++ b/stdlib/http/client.pyi
@@ -3,7 +3,7 @@ import io
 import ssl
 import sys
 import types
-from _typeshed import MaybeNone, ReadableBuffer, SupportsRead, SupportsReadline, WriteableBuffer
+from _typeshed import MaybeNone, ReadableBuffer, StrOrBytesPath, SupportsRead, SupportsReadline, WriteableBuffer
 from collections.abc import Callable, Iterable, Iterator, Mapping
 from email._policybase import _MessageT
 from socket import socket
@@ -243,8 +243,8 @@ class HTTPSConnection(HTTPConnection):
             self,
             host: str,
             port: int | None = None,
-            key_file: str | None = None,
-            cert_file: str | None = None,
+            key_file: StrOrBytesPath | None = None,
+            cert_file: StrOrBytesPath | None = None,
             timeout: float | None = ...,
             source_address: tuple[str, int] | None = None,
             *,
@@ -252,8 +252,8 @@ class HTTPSConnection(HTTPConnection):
             check_hostname: bool | None = None,
             blocksize: int = 8192,
         ) -> None: ...
-        key_file: str | None
-        cert_file: str | None
+        key_file: StrOrBytesPath | None
+        cert_file: StrOrBytesPath | None
 
 class HTTPException(Exception): ...
 
diff --git a/stdlib/imaplib.pyi b/stdlib/imaplib.pyi
index 6fe123519d63..3f0e23cd5852 100644
--- a/stdlib/imaplib.pyi
+++ b/stdlib/imaplib.pyi
@@ -1,7 +1,7 @@
 import subprocess
 import sys
 import time
-from _typeshed import ReadableBuffer, SizedBuffer, Unused
+from _typeshed import ReadableBuffer, SizedBuffer, StrOrBytesPath, Unused
 from builtins import list as _list  # conflicts with a method named "list"
 from collections.abc import Callable, Generator
 from datetime import datetime
@@ -120,9 +120,6 @@ if sys.version_info >= (3, 14):
         def burst(self, interval: float = 0.1) -> Generator[tuple[str, float | None]]: ...
 
 class IMAP4_SSL(IMAP4):
-    if sys.version_info < (3, 12):
-        keyfile: str
-        certfile: str
     if sys.version_info >= (3, 12):
         def __init__(
             self, host: str = "", port: int = 993, *, ssl_context: SSLContext | None = None, timeout: float | None = None
@@ -141,11 +138,13 @@ class IMAP4_SSL(IMAP4):
             self,
             host: str = "",
             port: int = 993,
-            keyfile: str | None = None,
-            certfile: str | None = None,
+            keyfile: StrOrBytesPath | None = None,
+            certfile: StrOrBytesPath | None = None,
             ssl_context: SSLContext | None = None,
             timeout: float | None = None,
         ) -> None: ...
+        keyfile: StrOrBytesPath | None
+        certfile: StrOrBytesPath | None
     sslobj: SSLSocket
     if sys.version_info >= (3, 14):
         @property
diff --git a/stdlib/poplib.pyi b/stdlib/poplib.pyi
index 658ff57e6040..0b5b7d26f206 100644
--- a/stdlib/poplib.pyi
+++ b/stdlib/poplib.pyi
@@ -1,6 +1,7 @@
 import socket
 import ssl
 import sys
+from _typeshed import StrOrBytesPath
 from builtins import list as _list  # conflicts with a method named "list"
 from re import Pattern
 from typing import Any, BinaryIO, Final, NoReturn, overload
@@ -71,11 +72,13 @@ class POP3_SSL(POP3):
             self,
             host: str,
             port: int = 995,
-            keyfile: str | None = None,
-            certfile: str | None = None,
+            keyfile: StrOrBytesPath | None = None,
+            certfile: StrOrBytesPath | None = None,
             timeout: float = ...,
             context: ssl.SSLContext | None = None,
         ) -> None: ...
+        keyfile: StrOrBytesPath | None
+        certfile: StrOrBytesPath | None
         # "context" is actually the last argument,
         # but that breaks LSP and it doesn't really matter because all the arguments are ignored
         def stls(self, context: Any = None, keyfile: Any = None, certfile: Any = None) -> NoReturn: ...
diff --git a/stdlib/smtplib.pyi b/stdlib/smtplib.pyi
index 431e8c8eea8a..03d56883e55e 100644
--- a/stdlib/smtplib.pyi
+++ b/stdlib/smtplib.pyi
@@ -1,6 +1,6 @@
 import sys
 from _socket import _Address as _SourceAddress
-from _typeshed import ReadableBuffer, SizedBuffer
+from _typeshed import ReadableBuffer, SizedBuffer, StrOrBytesPath
 from collections.abc import Sequence
 from email.message import Message as _Message
 from re import Pattern
@@ -139,7 +139,7 @@ class SMTP:
             "removed in Python 3.12. Use `context` parameter instead."
         )
         def starttls(
-            self, keyfile: str | None = None, certfile: str | None = None, context: SSLContext | None = None
+            self, keyfile: StrOrBytesPath | None = None, certfile: StrOrBytesPath | None = None, context: SSLContext | None = None
         ) -> _Reply: ...
 
     def sendmail(
@@ -196,14 +196,14 @@ class SMTP_SSL(SMTP):
             host: str = "",
             port: int = 0,
             local_hostname: str | None = None,
-            keyfile: str | None = None,
-            certfile: str | None = None,
+            keyfile: StrOrBytesPath | None = None,
+            certfile: StrOrBytesPath | None = None,
             timeout: float = ...,
             source_address: _SourceAddress | None = None,
             context: SSLContext | None = None,
         ) -> None: ...
-        keyfile: str | None
-        certfile: str | None
+        keyfile: StrOrBytesPath | None
+        certfile: StrOrBytesPath | None
 
 LMTP_PORT: Final = 2003
 

From d2dca339e7592010b5ae79f0ac9d3cbe6b565e47 Mon Sep 17 00:00:00 2001
From: donbarbos <donbarbos@proton.me>
Date: Sun, 11 Jan 2026 18:10:35 +0400
Subject: [PATCH 3/4] fix http.client *

---
 stdlib/http/client.pyi | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/stdlib/http/client.pyi b/stdlib/http/client.pyi
index e01c0165a151..19cee2ed0683 100644
--- a/stdlib/http/client.pyi
+++ b/stdlib/http/client.pyi
@@ -228,9 +228,9 @@ class HTTPSConnection(HTTPConnection):
             self,
             host: str,
             port: int | None = None,
+            *,
             timeout: float | None = ...,
             source_address: tuple[str, int] | None = None,
-            *,
             context: ssl.SSLContext | None = None,
             blocksize: int = 8192,
         ) -> None: ...

From 77c70edaf11ee48220c1e311fdacc1f149c7e24b Mon Sep 17 00:00:00 2001
From: donbarbos <donbarbos@proton.me>
Date: Mon, 12 Jan 2026 00:22:26 +0400
Subject: [PATCH 4/4] reflect the impossibility of passing context and "files"
 args at once

---
 stdlib/ftplib.pyi      |  6 ++++--
 stdlib/http/client.pyi |  5 ++++-
 stdlib/imaplib.pyi     | 10 ++++++++--
 stdlib/poplib.pyi      | 10 ++++++++--
 stdlib/smtplib.pyi     |  9 +++++----
 5 files changed, 29 insertions(+), 11 deletions(-)

diff --git a/stdlib/ftplib.pyi b/stdlib/ftplib.pyi
index 2558cbec7cd5..73eaa8a34e57 100644
--- a/stdlib/ftplib.pyi
+++ b/stdlib/ftplib.pyi
@@ -127,10 +127,12 @@ class FTP_TLS(FTP):
             user: str = "",
             passwd: str = "",
             acct: str = "",
-            *,
+            keyfile: None = None,
+            certfile: None = None,
             context: SSLContext | None = None,
             timeout: float | None = ...,
             source_address: tuple[str, int] | None = None,
+            *,
             encoding: str = "utf-8",
         ) -> None: ...
         @overload
@@ -146,7 +148,7 @@ class FTP_TLS(FTP):
             acct: str = "",
             keyfile: StrOrBytesPath | None = None,
             certfile: StrOrBytesPath | None = None,
-            context: SSLContext | None = None,
+            context: None = None,
             timeout: float | None = ...,
             source_address: tuple[str, int] | None = None,
             *,
diff --git a/stdlib/http/client.pyi b/stdlib/http/client.pyi
index 19cee2ed0683..699ef0e4c6d6 100644
--- a/stdlib/http/client.pyi
+++ b/stdlib/http/client.pyi
@@ -228,10 +228,13 @@ class HTTPSConnection(HTTPConnection):
             self,
             host: str,
             port: int | None = None,
-            *,
+            key_file: None = None,
+            cert_file: None = None,
             timeout: float | None = ...,
             source_address: tuple[str, int] | None = None,
+            *,
             context: ssl.SSLContext | None = None,
+            check_hostname: None = None,
             blocksize: int = 8192,
         ) -> None: ...
         @overload
diff --git a/stdlib/imaplib.pyi b/stdlib/imaplib.pyi
index 3f0e23cd5852..471530124f0c 100644
--- a/stdlib/imaplib.pyi
+++ b/stdlib/imaplib.pyi
@@ -127,7 +127,13 @@ class IMAP4_SSL(IMAP4):
     else:
         @overload
         def __init__(
-            self, host: str = "", port: int = 993, *, ssl_context: SSLContext | None = None, timeout: float | None = None
+            self,
+            host: str = "",
+            port: int = 993,
+            keyfile: None = None,
+            certfile: None = None,
+            ssl_context: SSLContext | None = None,
+            timeout: float | None = None,
         ) -> None: ...
         @overload
         @deprecated(
@@ -140,7 +146,7 @@ class IMAP4_SSL(IMAP4):
             port: int = 993,
             keyfile: StrOrBytesPath | None = None,
             certfile: StrOrBytesPath | None = None,
-            ssl_context: SSLContext | None = None,
+            ssl_context: None = None,
             timeout: float | None = None,
         ) -> None: ...
         keyfile: StrOrBytesPath | None
diff --git a/stdlib/poplib.pyi b/stdlib/poplib.pyi
index 0b5b7d26f206..f5669ec87e87 100644
--- a/stdlib/poplib.pyi
+++ b/stdlib/poplib.pyi
@@ -61,7 +61,13 @@ class POP3_SSL(POP3):
     else:
         @overload
         def __init__(
-            self, host: str, port: int = 995, *, timeout: float = ..., context: ssl.SSLContext | None = None
+            self,
+            host: str,
+            port: int = 995,
+            keyfile: None = None,
+            certfile: None = None,
+            timeout: float = ...,
+            context: ssl.SSLContext | None = None,
         ) -> None: ...
         @overload
         @deprecated(
@@ -75,7 +81,7 @@ class POP3_SSL(POP3):
             keyfile: StrOrBytesPath | None = None,
             certfile: StrOrBytesPath | None = None,
             timeout: float = ...,
-            context: ssl.SSLContext | None = None,
+            context: None = None,
         ) -> None: ...
         keyfile: StrOrBytesPath | None
         certfile: StrOrBytesPath | None
diff --git a/stdlib/smtplib.pyi b/stdlib/smtplib.pyi
index 03d56883e55e..74b5ea2cb6fc 100644
--- a/stdlib/smtplib.pyi
+++ b/stdlib/smtplib.pyi
@@ -132,14 +132,14 @@ class SMTP:
         def starttls(self, *, context: SSLContext | None = None) -> _Reply: ...
     else:
         @overload
-        def starttls(self, *, context: SSLContext | None = None) -> _Reply: ...
+        def starttls(self, keyfile: None = None, certfile: None = None, context: SSLContext | None = None) -> _Reply: ...
         @overload
         @deprecated(
             "The `keyfile`, `certfile` parameters are deprecated since Python 3.6; "
             "removed in Python 3.12. Use `context` parameter instead."
         )
         def starttls(
-            self, keyfile: StrOrBytesPath | None = None, certfile: StrOrBytesPath | None = None, context: SSLContext | None = None
+            self, keyfile: StrOrBytesPath | None = None, certfile: StrOrBytesPath | None = None, context: None = None
         ) -> _Reply: ...
 
     def sendmail(
@@ -181,7 +181,8 @@ class SMTP_SSL(SMTP):
             host: str = "",
             port: int = 0,
             local_hostname: str | None = None,
-            *,
+            keyfile: None = None,
+            certfile: None = None,
             timeout: float = ...,
             source_address: _SourceAddress | None = None,
             context: SSLContext | None = None,
@@ -200,7 +201,7 @@ class SMTP_SSL(SMTP):
             certfile: StrOrBytesPath | None = None,
             timeout: float = ...,
             source_address: _SourceAddress | None = None,
-            context: SSLContext | None = None,
+            context: None = None,
         ) -> None: ...
         keyfile: StrOrBytesPath | None
         certfile: StrOrBytesPath | None