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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-# due to outdated OpenSSL version in base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

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