diff --git a/security/py-pyopenssl/Makefile b/security/py-pyopenssl/Makefile
index 8666c21b4bf9..b3ad4902a0a2 100644
--- a/security/py-pyopenssl/Makefile
+++ b/security/py-pyopenssl/Makefile
@@ -1,50 +1,49 @@
 PORTNAME=	pyopenssl
-PORTVERSION=	25.3.0
-PORTREVISION=	1
+PORTVERSION=	26.0.0
 PORTEPOCH=	1
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	sunpoet@FreeBSD.org
 COMMENT=	Python interface to the OpenSSL library
 WWW=		https://www.pyopenssl.org/en/latest/ \
 		https://github.com/pyca/pyopenssl
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools>=0:devel/py-setuptools@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}wheel>=0:devel/py-wheel@${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 pep517 pytest pythonprefix
 
 NO_ARCH=	yes
 # 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_ENV=	LC_ALL=en_US.UTF-8 \
 		PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
 CPE_VENDOR=	jean-paul_calderone
 
 .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-pyopenssl/distinfo b/security/py-pyopenssl/distinfo
index c9a84165ae14..48701486f081 100644
--- a/security/py-pyopenssl/distinfo
+++ b/security/py-pyopenssl/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1759772426
-SHA256 (pyopenssl-25.3.0.tar.gz) = c981cb0a3fd84e8602d7afc209522773b94c1c2446a3c710a75b06fe1beae329
-SIZE (pyopenssl-25.3.0.tar.gz) = 184073
+TIMESTAMP = 1775587588
+SHA256 (pyopenssl-26.0.0.tar.gz) = f293934e52936f2e3413b89c6ce36df66a0b34ae1ea3a053b8c5020ff2f513fc
+SIZE (pyopenssl-26.0.0.tar.gz) = 185534