Index: head/devel/py-pytest/Makefile
===================================================================
--- head/devel/py-pytest/Makefile	(revision 501649)
+++ head/devel/py-pytest/Makefile	(revision 501650)
@@ -1,58 +1,57 @@
 # $FreeBSD$
 
 PORTNAME=	pytest
-PORTVERSION=	4.3.1
-PORTREVISION=	3
+PORTVERSION=	4.5.0
 CATEGORIES=	devel python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 
 MAINTAINER=	python@FreeBSD.org
 COMMENT=	Simple powerful testing with Python
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}setuptools_scm>=0:devel/py-setuptools_scm@${PY_FLAVOR}
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}atomicwrites>=1.0:devel/py-atomicwrites@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}attrs>=17.4.0:devel/py-attrs@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pluggy>=0.7:devel/py-pluggy@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pluggy>=0.9,<1.0:devel/py-pluggy@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}py>=1.5.0:devel/py-py@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}six>=1.10.0:devel/py-six@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}six>=1.10.0:devel/py-six@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}wcwidth>0:devel/py-wcwidth@${PY_FLAVOR}
 TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>0:devel/py-pytest@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}pexpect>0:misc/py-pexpect@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}pytest-xdist>=1.13:devel/py-pytest-xdist@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}hypothesis>=3.56:devel/py-hypothesis@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}nose>0:devel/py-nose@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}requests>0:www/py-requests@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}decorator>0:devel/py-decorator@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}requests>0:www/py-requests@${PY_FLAVOR}
 
 USES=		python
 USE_PYTHON=	autoplist concurrent distutils
 
 NO_ARCH=	yes
 
+py27_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR}
+
 .include <bsd.port.pre.mk>
 
-.if ${PYTHON_VER} >= 3.4
+.if ${PYTHON_VER} > 2.7
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}more-itertools>=4.0.0:devel/py-more-itertools@${PY_FLAVOR}
 .else
-RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}more-itertools5>=4.0.0:devel/py-more-itertools5@${PY_FLAVOR}
+RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}more-itertools5>=4.0.0,<6.0.0:devel/py-more-itertools5@${PY_FLAVOR}
 .endif
 
 .if ${PYTHON_VER} < 3.0
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}funcsigs>=0:devel/py-funcsigs@${PY_FLAVOR}
 .endif
 
 .if ${PYTHON_VER} < 3.6
 RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}pathlib2>=2.2.0:devel/py-pathlib2@${PY_FLAVOR}
 .endif
 
-.if ${PYTHON_VER} == 2.7
-TEST_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}mock>0:devel/py-mock@${PY_FLAVOR}
-.endif
+# test_cache_failure_warns fails
+# https://github.com/pytest-dev/pytest/issues/1845
 
 do-test:
-	@(cd ${TEST_WRKSRC} && ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest)
+	@(cd ${TEST_WRKSRC} && ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest -v -rs -k 'not test_cache_failure_warns')
 
 .include <bsd.port.post.mk>
Index: head/devel/py-pytest/distinfo
===================================================================
--- head/devel/py-pytest/distinfo	(revision 501649)
+++ head/devel/py-pytest/distinfo	(revision 501650)
@@ -1,3 +1,3 @@
-TIMESTAMP = 1553587773
-SHA256 (pytest-4.3.1.tar.gz) = 592eaa2c33fae68c7d75aacf042efc9f77b27c08a6224a4f59beab8d9a420523
-SIZE (pytest-4.3.1.tar.gz) = 917608
+TIMESTAMP = 1557834909
+SHA256 (pytest-4.5.0.tar.gz) = 1a8aa4fa958f8f451ac5441f3ac130d9fc86ea38780dd2715e6d5c5882700b24
+SIZE (pytest-4.5.0.tar.gz) = 943607
Index: head/devel/py-pytest/pkg-descr
===================================================================
--- head/devel/py-pytest/pkg-descr	(revision 501649)
+++ head/devel/py-pytest/pkg-descr	(revision 501650)
@@ -1,16 +1,12 @@
 The pytest testing tool makes it easy to write small tests, yet scales to
 support complex functional testing.
 
 Features:
 
-  * Auto-discovery of test modules and functions
   * Detailed info on failing assert statements
-  * Modular fixtures for managing small or parametrized long-lived test
-    resources
-  * Multi-paradigm support: you can use pytest to run test suites based on
-    unittest (or trial), nose
-  * Single-source compatibility from Python2.6 all the way up to Python3.4,
-    PyPy-2.3, (jython-2.5 untested)
-  * Many external plugins
+  * Auto-discovery of test modules and functions
+  * Modular fixtures to manage small or parametrized long-lived test resources
+  * Can run unittest (or trial), nose test suites out of the box
+  * Rich plugin architecture, with over 315+ external plugins
 
 WWW: https://docs.pytest.org/en/latest/