diff --git a/security/py-openssl/Makefile b/security/py-openssl/Makefile
--- a/security/py-openssl/Makefile
+++ b/security/py-openssl/Makefile
@@ -1,5 +1,5 @@
 PORTNAME=	openssl
-DISTVERSION=	21.0.0
+PORTVERSION=	23.2.0
 PORTEPOCH=	1
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
@@ -13,40 +13,34 @@
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}six>=1.5.2:devel/py-six@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>=3.0.1:devel/py-pytest@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}flaky>0:devel/py-flaky@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pretend>0:devel/py-pretend@${PY_FLAVOR} \
 		${LOCALBASE}/share/certs/ca-root-nss.crt:security/ca_root_nss
 
 USES=		cpe python pycryptography:run
-USE_PYTHON=	autoplist concurrent distutils pythonprefix
+USE_PYTHON=	autoplist concurrent distutils pytest pythonprefix
 
 NO_ARCH=	yes
 
 CPE_VENDOR=	jean-paul_calderone
 CPE_PRODUCT=	py${PORTNAME}
 
-# Use options.mk to use OSVERSION and handle redefine PORTEPOCH
-.include <bsd.port.options.mk>
-
-# We need to keep old py-cryptography and py-penssl for 11.x release
-# due to outdated OpenSSL version in base
-
 # 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.
-do-test:
-	@cd ${WRKSRC} && ${SET_ENV} LC_ALL=en_US.UTF-8 ${TEST_ENV} \
-			PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR} \
-			${PYTHON_CMD} -m pytest -rs -v -k \
-			'not test_connect_refused and \
-		       	not test_set_verify_callback_exception'
+PYTEST_IGNORED_TESTS=	test_connect_ex \
+			test_connect_refused \
+			test_set_verify_callback_exception
+TEST_ENV=	LC_ALL=en_US.UTF-8 \
+		PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
 .include <bsd.port.mk>
diff --git a/security/py-openssl/distinfo b/security/py-openssl/distinfo
--- a/security/py-openssl/distinfo
+++ b/security/py-openssl/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1673046083
-SHA256 (pyOpenSSL-21.0.0.tar.gz) = 5e2d8c5e46d0d865ae933bef5230090bdaf5506281e9eec60fa250ee80600cb3
-SIZE (pyOpenSSL-21.0.0.tar.gz) = 175652
+TIMESTAMP = 1691096194
+SHA256 (pyOpenSSL-23.2.0.tar.gz) = 276f931f55a452e7dea69c7173e984eb2a4407ce413c918aa34b55f82f9b8bac
+SIZE (pyOpenSSL-23.2.0.tar.gz) = 185132