diff --git a/www/py-cherrypy/Makefile b/www/py-cherrypy/Makefile
index 37a9cac79395..4c79242f725c 100644
--- a/www/py-cherrypy/Makefile
+++ b/www/py-cherrypy/Makefile
@@ -1,60 +1,58 @@
 PORTNAME=	cherrypy
-PORTVERSION=	17.4.2
-PORTREVISION=	2
+PORTVERSION=	18.8.0
+PORTREVISION=	0
 CATEGORIES=	www python
 MASTER_SITES=	PYPI
 PKGNAMEPREFIX=	${PYTHON_PKGNAMEPREFIX}
 DISTNAME=	CherryPy-${PORTVERSION}
 
-PATCH_SITES=	https://github.com/${PORTNAME}/${PORTNAME}/commit/
-PATCHFILES+=	8245a74aa4e0.patch:-p1 # https://github.com/cherrypy/cherrypy/pull/1945
-
 MAINTAINER=	nivit@FreeBSD.org
 COMMENT=	Pythonic, object-oriented web development framework
 WWW=		http://www.cherrypy.org/
 
 LICENSE=	BSD3CLAUSE
 
 BUILD_DEPENDS=	${PYTHON_PKGNAMEPREFIX}pip>0:devel/py-pip@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}setuptools_scm>0:devel/py-setuptools_scm@${PY_FLAVOR}
-RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}six>=1.11.0:devel/py-six@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}cheroot>=6.2.4:www/py-cheroot@${PY_FLAVOR} \
+RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cheroot>=8.2.1:www/py-cheroot@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}jaraco.collections>=4.2.0:devel/py-jaraco.collections@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}more-itertools>0:devel/py-more-itertools@${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} \
+		${PYTHON_PKGNAMEPREFIX}six>=1.11.0:devel/py-six@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}zclockfile>0:devel/py-zclockfile@${PY_FLAVOR}
+TEST_DEPENDS=	${PYTHON_PKGNAMEPREFIX}codecov>=2.1.13:devel/py-codecov@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}coverage>=7.2.2:devel/py-coverage@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}objgraph>=3.5.0:devel/py-objgraph@${PY_FLAVOR} \
 		${PYTHON_PKGNAMEPREFIX}path.py>0:devel/py-path.py@${PY_FLAVOR} \
-		${PYTHON_PKGNAMEPREFIX}requests-toolbelt>0:www/py-requests-toolbelt@${PY_FLAVOR}
+		${PYTHON_PKGNAMEPREFIX}pytest-cov>=2.9.0:devel/py-pytest-cov@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pytest-forked>=1.6.0:devel/py-pytest-forked@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pytest-services>=2:devel/py-pytest-services@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}pytest-sugar>=0.9.7:devel/py-pytest-sugar@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}python-memcached>=1.59:databases/py-python-memcached@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}requests-toolbelt>0:www/py-requests-toolbelt@${PY_FLAVOR} \
+		${PYTHON_PKGNAMEPREFIX}setuptools>0:devel/py-setuptools@${PY_FLAVOR}
 
 USES=		cpe python:3.6+
-USE_PYTHON=	distutils autoplist concurrent
-
-TEST_ENV=	PYTHONPATH=${STAGEDIR}${PYTHONPREFIX_SITELIBDIR}
-
+USE_PYTHON=	autoplist concurrent distutils pytest
+PYTEST_BROKEN_TESTS=	test_0_NormalStateFlow test_8_Ram_Cleanup \
+			test_multipart_decoding \
+			test_multipart_decoding_bigger_maxrambytes test_pass \
+			test_4_File_deletion test_3_Redirect \
+			test_threadlocal_garbage
 NO_ARCH=	yes
 PORTEXAMPLES=	*
 
 OPTIONS_DEFINE=	EXAMPLES
 
-EXAMPLES_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}sqlobject>=1.5.1:databases/py-sqlobject@${PY_FLAVOR} \
-			${PYTHON_PKGNAMEPREFIX}cheetah3>0:devel/py-cheetah3@${PY_FLAVOR}
+EXAMPLES_RUN_DEPENDS=	${PYTHON_PKGNAMEPREFIX}cheetah3>0:devel/py-cheetah3@${PY_FLAVOR} \
+			${PYTHON_PKGNAMEPREFIX}sqlobject>=1.5.1:databases/py-sqlobject@${PY_FLAVOR}
 
 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}/,,})
 
-# 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/distinfo b/www/py-cherrypy/distinfo
index 4bcd9f8d43b9..cb3dafdf9fae 100644
--- a/www/py-cherrypy/distinfo
+++ b/www/py-cherrypy/distinfo
@@ -1,5 +1,3 @@
-TIMESTAMP = 1597378048
-SHA256 (CherryPy-17.4.2.tar.gz) = ef1619ad161f526745d4f0e4e517753d9d985814f1280e330661333d2ba05cdf
-SIZE (CherryPy-17.4.2.tar.gz) = 684366
-SHA256 (8245a74aa4e0.patch) = 8e3bbc5bf39cdb005a88568f22e0193ccbe96dcf4882c9a26bf38e2f74bd077c
-SIZE (8245a74aa4e0.patch) = 1114
+TIMESTAMP = 1686603836
+SHA256 (CherryPy-18.8.0.tar.gz) = 9b48cfba8a2f16d5b6419cc657e6d51db005ba35c5e3824e4728bb03bbc7ef9b
+SIZE (CherryPy-18.8.0.tar.gz) = 622679
diff --git a/www/py-cherrypy/files/patch-cherrypy_lib_sessions.py b/www/py-cherrypy/files/patch-cherrypy_lib_sessions.py
deleted file mode 100644
index 8130d1130c5c..000000000000
--- a/www/py-cherrypy/files/patch-cherrypy_lib_sessions.py
+++ /dev/null
@@ -1,27 +0,0 @@
-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
deleted file mode 100644
index d06d636f7de7..000000000000
--- a/www/py-cherrypy/files/patch-setup.py
+++ /dev/null
@@ -1,17 +0,0 @@
-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': [