Index: security/py-openssl/Makefile
===================================================================
--- security/py-openssl/Makefile
+++ security/py-openssl/Makefile
@@ -1,6 +1,5 @@
 PORTNAME=	openssl
-DISTVERSION=	21.0.0
-PORTEPOCH=	1
+PORTVERSION=	23.2.0
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -19,7 +18,7 @@
 		${PYTHON_PKGNAMEPREFIX}pretend>0:devel/py-pretend@${PY_FLAVOR} \
 		${LOCALBASE}/share/certs/ca-root-nss.crt:security/ca_root_nss
 
-USES=		cpe python pycryptography:run
+USES=		cpe python pycryptography:run pytest
 USE_PYTHON=	autoplist concurrent distutils pythonprefix
 
 NO_ARCH=	yes
@@ -27,8 +26,9 @@
 CPE_VENDOR=	jean-paul_calderone
 CPE_PRODUCT=	py${PORTNAME}
 
-# Use options.mk to use OSVERSION and handle redefine PORTEPOCH
-.include <bsd.port.options.mk>
+TEST_ENV+=	\
+	LC_ALL=en_US.UTF-8 \
+	PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
 # We need to keep old py-cryptography and py-penssl for 11.x release
 # due to outdated OpenSSL version in base
@@ -39,14 +39,13 @@
 #   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_ARGS+= \
+	-rs -v \
+	-k 'not test_connect_refused and not test_set_verify_callback_exception and not test_connect_ex'
 
 .include <bsd.port.mk>
Index: security/py-openssl/distinfo
===================================================================
--- security/py-openssl/distinfo
+++ 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 = 1691200004
+SHA256 (pyOpenSSL-23.2.0.tar.gz) = 276f931f55a452e7dea69c7173e984eb2a4407ce413c918aa34b55f82f9b8bac
+SIZE (pyOpenSSL-23.2.0.tar.gz) = 185132