diff --git a/security/py-openssl/Makefile b/security/py-openssl/Makefile
index c708b56d4d53..79371eeebbd4 100644
--- a/security/py-openssl/Makefile
+++ b/security/py-openssl/Makefile
@@ -1,53 +1,53 @@
 # Created by: ijliao
 
 PORTNAME=	openssl
-PORTVERSION=	20.0.1
+PORTVERSION=	22.0.0
 CATEGORIES=	security python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	pyOpenSSL-${PORTVERSION}
 
 MAINTAINER=	sbz@FreeBSD.org
 COMMENT=	Python interface to the OpenSSL library
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cryptography>=2.8:security/py-cryptography@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}six>=1.5.2:devel/py-six@${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:3.6+
 USE_PYTHON=	autoplist concurrent distutils 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 # due to outdated OpenSSL version in base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
 #
 # 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'
 
 .include <bsd.port.mk>
diff --git a/security/py-openssl/distinfo b/security/py-openssl/distinfo
index 5fe3a9600094..5e3728a1af4f 100644
--- a/security/py-openssl/distinfo
+++ b/security/py-openssl/distinfo
@@ -1,5 +1,3 @@
-TIMESTAMP = 1613747780
-SHA256 (pyOpenSSL-19.1.0.tar.gz) = 9a24494b2602aaf402be5c9e30a0b82d4a5c67528fe8fb475e3f3bc00dd69507
-SIZE (pyOpenSSL-19.1.0.tar.gz) = 160510
-SHA256 (pyOpenSSL-20.0.1.tar.gz) = 4c231c759543ba02560fcd2480c48dcec4dae34c9da7d3747c508227e0624b51
-SIZE (pyOpenSSL-20.0.1.tar.gz) = 173736
+TIMESTAMP = 1647962240
+SHA256 (pyOpenSSL-22.0.0.tar.gz) = 660b1b1425aac4a1bea1d94168a85d99f0b3144c869dd4390d27629d0087f1bf
+SIZE (pyOpenSSL-22.0.0.tar.gz) = 178438