Index: head/security/py-openssl/Makefile
===================================================================
--- head/security/py-openssl/Makefile	(revision 508145)
+++ head/security/py-openssl/Makefile	(revision 508146)
@@ -1,39 +1,55 @@
 # Created by: ijliao
 # $FreeBSD$
 
 PORTNAME=	openssl
-PORTVERSION=	18.0.0
+PORTVERSION=	19.0.0
 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=	${PYTHON_PKGNAMEPREFIX}cryptography>=2.2.1:security/py-cryptography@${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
 
-OPTIONS_DEFINE=	EXAMPLES
-
 USES=		cpe python
 USE_PYTHON=	autoplist concurrent distutils pythonprefix
 
 NO_ARCH=	yes
 
 CPE_VENDOR=	jean-paul_calderone
 CPE_PRODUCT=	py${PORTNAME}
 
 PORTEXAMPLES=	*
 
+OPTIONS_DEFINE=	EXAMPLES
+
 post-install-EXAMPLES-on:
 	@${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	(cd ${WRKSRC}/examples/ && ${COPYTREE_SHARE} . ${STAGEDIR}${EXAMPLESDIR})
 
+# 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} && ${PYTHON_CMD} ${PYSETUP} test)
+	@cd ${WRKSRC} && \
+		${SET_ENV} LC_ALL=en_US.UTF-8 ${PYTHON_CMD} -m pytest -rs -v -k ' \
+	       		not test_connect_refused and \
+		       	not test_set_verify_callback_exception'
 
 .include <bsd.port.mk>
Index: head/security/py-openssl/distinfo
===================================================================
--- head/security/py-openssl/distinfo	(revision 508145)
+++ head/security/py-openssl/distinfo	(revision 508146)
@@ -1,3 +1,3 @@
 TIMESTAMP = 1540136888
-SHA256 (pyOpenSSL-18.0.0.tar.gz) = 6488f1423b00f73b7ad5167885312bb0ce410d3312eb212393795b53c8caa580
-SIZE (pyOpenSSL-18.0.0.tar.gz) = 167296
+SHA256 (pyOpenSSL-19.0.0.tar.gz) = aeca66338f6de19d1aa46ed634c3b9ae519a64b458f8468aec688e7e3c20f200
+SIZE (pyOpenSSL-19.0.0.tar.gz) = 168551