Index: security/py-openssl/Makefile
===================================================================
--- security/py-openssl/Makefile
+++ security/py-openssl/Makefile
@@ -1,6 +1,5 @@
 PORTNAME=	openssl
-PORTVERSION=	20.0.1
-PORTEPOCH=	1
+PORTVERSION=	23.0.0
 CATEGORIES=	security python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
@@ -20,7 +19,7 @@
 		${PYTHON_PKGNAMEPREFIX}pretend>0:devel/py-pretend@${PY_FLAVOR} \
 		${LOCALBASE}/share/certs/ca-root-nss.crt:security/ca_root_nss
 
-USES=		cpe python:3.6+
+USES=		cpe python:3.6+ pytest
 USE_PYTHON=	autoplist concurrent distutils pythonprefix
 
 NO_ARCH=	yes
@@ -28,8 +27,9 @@
 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 # due to outdated OpenSSL version in base
@@ -43,11 +43,8 @@
 #
 # 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'
 
 .include <bsd.port.mk>
Index: security/py-openssl/distinfo
===================================================================
--- security/py-openssl/distinfo
+++ security/py-openssl/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1648120923
-SHA256 (pyOpenSSL-20.0.1.tar.gz) = 4c231c759543ba02560fcd2480c48dcec4dae34c9da7d3747c508227e0624b51
-SIZE (pyOpenSSL-20.0.1.tar.gz) = 173736
+TIMESTAMP = 1678684712
+SHA256 (pyOpenSSL-23.0.0.tar.gz) = c1cc5f86bcacefc84dada7d31175cae1b1518d5f60d3d0bb595a67822a868a6f
+SIZE (pyOpenSSL-23.0.0.tar.gz) = 182375