diff --git a/security/py-openssl/Makefile b/security/py-openssl/Makefile
index 1ef38f194a0b..6caad225ba2b 100644
--- a/security/py-openssl/Makefile
+++ b/security/py-openssl/Makefile
@@ -1,46 +1,50 @@
 PORTNAME=	openssl
-PORTVERSION=	25.0.0
-PORTREVISION=	1
+PORTVERSION=	25.3.0
 PORTEPOCH=	1
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	pyopenssl-${PORTVERSION}
 
-MAINTAINER=	sbz@FreeBSD.org
+MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Python interface to the OpenSSL library
 WWW=		https://github.com/pyca/pyopenssl
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}typing-extensions>=4.9:devel/py-typing-extensions@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pretend>0:devel/py-pretend@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-rerunfailures>0:devel/py-pytest-rerunfailures@${PY_FLAVOR}
 
 USES=		cpe python
 USE_PYTHON=	autoplist concurrent cryptography distutils pytest pythonprefix
 
 NO_ARCH=	yes
 
 CPE_VENDOR=	jean-paul_calderone
 CPE_PRODUCT=	py${PORTNAME}
 
 # These tests will be skipped due the following reasons:
 #
 # * test_connect_refused: Avoid stalling in build environments that don't have
 #   a internet connection
 # * test_set_verify_callback_exception: Fails on *BSD systems, see also
 #   https://github.com/pyca/pyopenssl/issues/656 for further details
 # * test_connect_ex: succeeds unexpectedly:
 #   https://github.com/pyca/pyopenssl/issues/1192
 #
 # The system clock must be in sync otherwise the test "test_verify_with_time"
 # will fail.
 PYTEST_IGNORED_TESTS=	test_connect_ex \
 			test_connect_refused \
 			test_set_verify_callback_exception
 TEST_ENV=	LC_ALL=en_US.UTF-8 \
 		PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
-.include <bsd.port.mk>
+.include <bsd.port.pre.mk>
+
+.if ${PYTHON_REL} < 31300
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}typing-extensions>=4.9:devel/py-typing-extensions@${PY_FLAVOR}
+.endif
+
+.include <bsd.port.post.mk>
diff --git a/security/py-openssl/distinfo b/security/py-openssl/distinfo
index 9b3c208d9347..c9a84165ae14 100644
--- a/security/py-openssl/distinfo
+++ b/security/py-openssl/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1739473917
-SHA256 (pyopenssl-25.0.0.tar.gz) = cd2cef799efa3936bb08e8ccb9433a575722b9dd986023f1cabc4ae64e9dac16
-SIZE (pyopenssl-25.0.0.tar.gz) = 179573
+TIMESTAMP = 1759772426
+SHA256 (pyopenssl-25.3.0.tar.gz) = c981cb0a3fd84e8602d7afc209522773b94c1c2446a3c710a75b06fe1beae329
+SIZE (pyopenssl-25.3.0.tar.gz) = 184073