diff --git a/www/py-cherrypy/Makefile b/www/py-cherrypy/Makefile
index 9e9c1b357292..18393c8fce00 100644
--- a/www/py-cherrypy/Makefile
+++ b/www/py-cherrypy/Makefile
@@ -1,53 +1,58 @@
 # Created by: Nicola Vitale	<nivit@email.it>
 
 PORTNAME=	cherrypy
 PORTVERSION=	17.4.2
+PORTREVISION=	1
 CATEGORIES=	www python
 MASTER_SITES=	CHEESESHOP
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	CherryPy-${PORTVERSION}
 
 MAINTAINER=	nivit@FreeBSD.org
 COMMENT=	Pythonic, object-oriented web development framework
 
 LICENSE=	BSD3CLAUSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pip>0:devel/py-pip@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools_scm>0:devel/py-setuptools_scm@${PY_FLAVOR}
-
-EXAMPLES_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sqlobject>=1.5.1:databases/py-sqlobject@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}cheetah3>0:devel/py-cheetah3@${PY_FLAVOR}
-EXAMPLESDIR=	${PREFIX}/share/examples/${PKGNAMEPREFIX}${PORTNAME}
-
 RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}six>=1.11.0:devel/py-six@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}cheroot>=6.2.4:www/py-cheroot@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}portend>=2.1.1:net/py-portend@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}zclockfile>0:devel/py-zclockfile@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}more-itertools>0:devel/py-more-itertools@${PY_FLAVOR}
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pytest>=2.8:devel/py-pytest@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}path.py>0:devel/py-path.py@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}requests-toolbelt>0:www/py-requests-toolbelt@${PY_FLAVOR}
 
-OPTIONS_DEFINE=	EXAMPLES
+USES=		python:3.6+
+USE_PYTHON=	distutils autoplist concurrent
+
+TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
 
+NO_ARCH=	yes
 PORTEXAMPLES=	*
 
-USES=		python:3.6+
-USE_PYTHON=	distutils autoplist concurrent
+OPTIONS_DEFINE=	EXAMPLES
 
-.include <bsd.port.options.mk>
+EXAMPLES_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sqlobject>=1.5.1:databases/py-sqlobject@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}cheetah3>0:devel/py-cheetah3@${PY_FLAVOR}
 
-.if ${PORT_OPTIONS:MEXAMPLES}
-post-install:
+post-install-EXAMPLES-on:
 	@${MKDIR} ${STAGEDIR}${EXAMPLESDIR}
 	(cd ${WRKSRC}/cherrypy/tutorial && \
 	${COPYTREE_SHARE} . ${STAGEDIR}${EXAMPLESDIR})
 	(cd ${STAGEDIR}${PREFIX} && \
 	${PYTHON_CMD} ${PYTHON_LIBDIR}/compileall.py \
 		-d ${EXAMPLESDIR} ${EXAMPLESDIR:S,${PREFIX}/,,})
-.endif
-
-.include <bsd.port.pre.mk>
-
-.if ${PYTHON_REL} < 3800
-RUN_DEPENDS+=	${PYTHON_PKGNAMEPREFIX}contextlib2>0:devel/py-contextlib2@${PY_FLAVOR}
-.endif
 
-.include <bsd.port.post.mk>
+# Some tests fails with Python 3.6/3.7/3.8/3.9 and are omitted for now.
+# This should be revised once the ports gets updated to a newer release.
+do-test:
+	@cd ${TEST_WRKSRC} && ${SETENV} ${TEST_ENV} ${PYTHON_CMD} -m pytest -v -rs \
+		-o addopts='' \
+		-k 'not test_HTTP11_Timeout_after_request \
+		and not test_threadlocal_garbage \
+		and not test_null_bytes \
+		and not testCombinedTools'
+
+.include <bsd.port.mk>
diff --git a/www/py-cherrypy/files/patch-cherrypy_lib_sessions.py b/www/py-cherrypy/files/patch-cherrypy_lib_sessions.py
new file mode 100644
index 000000000000..8130d1130c5c
--- /dev/null
+++ b/www/py-cherrypy/files/patch-cherrypy_lib_sessions.py
@@ -0,0 +1,27 @@
+Remove contextlib2 and use contextlib from the standard library.
+
+* Contextlib has been in the Python standard library since Python 3.2.
+* Contextlib2 is a backport to Python 2 (and is supported through Python 3.7).
+
+Obtained from: https://github.com/cherrypy/cherrypy/commit/2fc78dc9af3e
+
+--- cherrypy/lib/sessions.py.orig	2021-04-22 13:06:39 UTC
++++ cherrypy/lib/sessions.py
+@@ -109,7 +109,7 @@ import binascii
+
+ import six
+ from six.moves import cPickle as pickle
+-import contextlib2
++import contextlib
+
+ import zc.lockfile
+
+@@ -572,7 +572,7 @@ class FileSession(Session):
+     def release_lock(self, path=None):
+         """Release the lock on the currently-loaded session data."""
+         self.lock.close()
+-        with contextlib2.suppress(FileNotFoundError):
++        with contextlib.suppress(FileNotFoundError):
+             os.remove(self.lock._path)
+         self.locked = False
+
diff --git a/www/py-cherrypy/files/patch-setup.py b/www/py-cherrypy/files/patch-setup.py
new file mode 100644
index 000000000000..d06d636f7de7
--- /dev/null
+++ b/www/py-cherrypy/files/patch-setup.py
@@ -0,0 +1,17 @@
+Remove contextlib2 and use contextlib from the standard library.
+
+* Contextlib has been in the Python standard library since Python 3.2.
+* Contextlib2 is a backport to Python 2 (and is supported through Python 3.7).
+
+Obtained from: https://github.com/cherrypy/cherrypy/commit/2fc78dc9af3e
+
+--- setup.py.orig	2021-04-22 13:05:31 UTC
++++ setup.py
+@@ -66,7 +66,6 @@ params = dict(
+         'portend>=2.1.1',
+         'more_itertools',
+         'zc.lockfile',
+-        'contextlib2',
+     ],
+     extras_require={
+         'docs': [