diff --git a/package/python-pyopenssl/0001-CVE-2026-27448.patch b/package/python-pyopenssl/0001-CVE-2026-27448.patch
new file mode 100644
index 0000000000..e2940fc168
--- /dev/null
+++ b/package/python-pyopenssl/0001-CVE-2026-27448.patch
@@ -0,0 +1,50 @@
+From d41a814759a9fb49584ca8ab3f7295de49a85aa0 Mon Sep 17 00:00:00 2001
+From: Alex Gaynor <alex.gaynor@gmail.com>
+Date: Mon, 16 Feb 2026 21:04:37 -0500
+Subject: [PATCH] Handle exceptions in set_tlsext_servername_callback callbacks
+ (#1478)
+
+When the servername callback raises an exception, call sys.excepthook
+with the exception info and return SSL_TLSEXT_ERR_ALERT_FATAL to abort
+the handshake. Previously, exceptions would propagate uncaught through
+the CFFI callback boundary.
+
+https://claude.ai/code/session_01P7y1XmWkdtC5UcmZwGDvGi
+
+Co-authored-by: Claude <noreply@anthropic.com>
+
+Upstream: https://github.com/pyca/pyopenssl/commit/d41a814759a9fb49584ca8ab3f7295de49a85aa0
+CVE: CVE-2026-27448
+[thomas: backported, stripped tests and changelog]
+Signed-off-by: Thomas Perale <thomas.perale@mind.be>
+---
+ src/OpenSSL/SSL.py |  7 ++++++-
+ 1 files changed, 7 insertions(+)
+ 
+diff --git a/src/OpenSSL/SSL.py b/src/OpenSSL/SSL.py
+index 4db5240..a6263c4 100644
+--- a/src/OpenSSL/SSL.py
++++ b/src/OpenSSL/SSL.py
+@@ -2,6 +2,7 @@
+ 
+ import os
+ import socket
++import sys
+ import typing
+ import warnings
+ from collections.abc import Sequence
+@@ -1686,7 +1687,11 @@ class Context:
+ 
+         @wraps(callback)
+         def wrapper(ssl, alert, arg):  # type: ignore[no-untyped-def]
+-            callback(Connection._reverse_mapping[ssl])
++            try:
++                callback(Connection._reverse_mapping[ssl])
++            except Exception:
++                sys.excepthook(*sys.exc_info())
++                return _lib.SSL_TLSEXT_ERR_ALERT_FATAL
+             return 0
+ 
+         self._tlsext_servername_callback = _ffi.callback(
+-- 
+2.43.0
diff --git a/package/python-pyopenssl/0002-CVE-2026-27459.patch b/package/python-pyopenssl/0002-CVE-2026-27459.patch
new file mode 100644
index 0000000000..586c443093
--- /dev/null
+++ b/package/python-pyopenssl/0002-CVE-2026-27459.patch
@@ -0,0 +1,46 @@
+From 57f09bb4bb051d3bc2a1abd36e9525313d5cd408 Mon Sep 17 00:00:00 2001
+From: Alex Gaynor <alex.gaynor@gmail.com>
+Date: Wed, 18 Feb 2026 07:46:15 -0500
+Subject: [PATCH] Fix buffer overflow in DTLS cookie generation callback
+ (#1479)
+
+The cookie generate callback copied user-returned bytes into a
+fixed-size native buffer without enforcing a maximum length. A
+callback returning more than DTLS1_COOKIE_LENGTH bytes would overflow
+the OpenSSL-provided buffer, corrupting adjacent memory.
+
+Co-authored-by: Claude Opus 4.6 <noreply@anthropic.com>
+
+Upstream: https://github.com/pyca/pyopenssl/commit/57f09bb4bb051d3bc2a1abd36e9525313d5cd408
+CVE: CVE-2026-27459
+[thomas: backported, stripped tests and changelog]
+Signed-off-by: Thomas Perale <thomas.perale@mind.be>
+---
+ src/OpenSSL/SSL.py |  7 +++++++
+ 1 files changed, 7 insertions(+)
+ 
+diff --git a/src/OpenSSL/SSL.py b/src/OpenSSL/SSL.py
+index a6263c4..2e4da78 100644
+--- a/src/OpenSSL/SSL.py
++++ b/src/OpenSSL/SSL.py
+@@ -716,11 +716,18 @@ class _CookieGenerateCallbackHelper(_CallbackExceptionHelper):
+     def __init__(self, callback: _CookieGenerateCallback) -> None:
+         _CallbackExceptionHelper.__init__(self)
+ 
++        max_cookie_len = getattr(_lib, "DTLS1_COOKIE_LENGTH", 255)
++
+         @wraps(callback)
+         def wrapper(ssl, out, outlen):  # type: ignore[no-untyped-def]
+             try:
+                 conn = Connection._reverse_mapping[ssl]
+                 cookie = callback(conn)
++                if len(cookie) > max_cookie_len:
++                    raise ValueError(
++                        f"Cookie too long (got {len(cookie)} bytes, "
++                        f"max {max_cookie_len})"
++                    )
+                 out[0 : len(cookie)] = cookie
+                 outlen[0] = len(cookie)
+                 return 1
+-- 
+2.43.0
diff --git a/package/python-pyopenssl/python-pyopenssl.mk b/package/python-pyopenssl/python-pyopenssl.mk
index 33884f8d6c..2e1e93cb7e 100644
--- a/package/python-pyopenssl/python-pyopenssl.mk
+++ b/package/python-pyopenssl/python-pyopenssl.mk
@@ -13,4 +13,10 @@ PYTHON_PYOPENSSL_CPE_ID_VENDOR = pyopenssl
 PYTHON_PYOPENSSL_CPE_ID_PRODUCT = pyopenssl
 PYTHON_PYOPENSSL_SETUP_TYPE = setuptools
 
+# 0001-CVE-2026-27448.patch
+PYTHON_PYOPENSSL_IGNORE_CVES += CVE-2026-27448
+
+# 0002-CVE-2026-27459.patch
+PYTHON_PYOPENSSL_IGNORE_CVES += CVE-2026-27459
+
 $(eval $(python-package))